ethyl 2-iodobenzoate

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Isopropyl-4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-7-ylamine (Compound 45, 500 mg, 2.152 mmol) was placed into the round bottom flask charged with argon. Pd2 (dab)3 (4.926 mg, 0.25 mol %), and BINAP (10.05 mg, 0.75 mol %) were added, followed by NaOtBu (405.27 mg, 3.012 mmol), ethyl iodobenzoate (831.7 mg, 3.012 mmol) and toluene (8 mL). The resulting mixture was stirred at 80° C. for 3 days, cooled to room temperature, and filtered through Celite. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.26) to give the title compound (642.76 mg, 79%) as a pale yellow solid: charged with argon cooled to room temperature filtered through Celite The filtrate was concentrated under reduced pressure the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.26)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7-Amino-1-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydroquinoline (Compound 33, 130 mg, 0.5954 mmol) was placed into the round bottom flask charged with argon and Pd2 (dab)3 (1.363 mg, 0.25 mol %), and BINAP (2.78 mg, 0.75 mol %) were added, followed by addition of NaOtBu (80.11 mg, 0.8335 mmol), ethyl iodobenzoate (230 mg, 0.8335 mmol) and toluene (3 mL). The resulting mixture was stirred at 80° C. for 3 days, cooled to room temperature, and filtered through Celite. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.30) to give the title compound (90.3 mg, 41%) as a solid: PNMR (300 MHz, CDCl3): δ1.20 (d, 6 H, J=6.6 Hz), 1.28 (s, 6 H), 1.38 (t, 3 H, J=7.1 Hz), 1.71 (t, 2 H, J=6.0 Hz), 3.19 (t, 2 H, J=6.0 Hz), 4.02 (sp, 1 H, J=6.6 Hz), 4.34 (q, 2 H, J=7.1 Hz), 5.92 (s, 1 H), 6.43 (dd, 1 H, J=8.1, 2.1 Hz), 6.50 (d, 1 H, J=2.1 Hz), 6.97 (d, 2 H, J=8.7 Hz), 7.14 (d, 1 H, J=8.1 Hz), 7.90 (d, 2 H, J=8.7 Hz). were added cooled to room temperature filtered through Celite The filtrate was concentrated under reduced pressure the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.30)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Isopropyl-4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-7-ylamine (Compound 45, 500 mg, 2.152 mmol) was placed into the round bottom flask charged with argon. Pd2 (dab)3 (4.926 mg, 0.25 mol %), and BINAP (10.05 mg, 0.75 mol %) were added, followed by NaOtBu (405.27 mg, 3.012 mmol), ethyl iodobenzoate (831.7 mg, 3.012 mmol) and toluene (8 mL). The resulting mixture was stirred at 80° C. for 3 days, cooled to room temperature, and filtered through Celite. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.26) to give the title compound (642.76 mg, 79%) as a pale yellow solid: charged with argon cooled to room temperature filtered through Celite The filtrate was concentrated under reduced pressure the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.26)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Isopropyl-4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-7-ylamine (Compound 45, 500 mg, 2.152 mmol) was placed into the round bottom flask charged with argon. Pd2 (dab)3 (4.926 mg, 0.25 mol %), and BINAP (10.05 mg, 0.75 mol %) were added, followed by NaOtBu (405.27 mg, 3.012 mmol), ethyl iodobenzoate (831.7 mg, 3.012 mmol) and toluene (8 mL). The resulting mixture was stirred at 80° C. for 3 days, cooled to room temperature, and filtered through Celite. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.26) to give the title compound (642.76 mg, 79%) as a pale yellow solid: charged with argon cooled to room temperature filtered through Celite The filtrate was concentrated under reduced pressure the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.26)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7-Amino-1-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydroquinoline (Compound 33, 130 mg, 0.5954 mmol) was placed into the round bottom flask charged with argon and Pd2 (dab)3 (1.363 mg, 0.25 mol %), and BINAP (2.78 mg, 0.75 mol %) were added, followed by addition of NaOtBu (80.11 mg, 0.8335 mmol), ethyl iodobenzoate (230 mg, 0.8335 mmol) and toluene (3 mL). The resulting mixture was stirred at 80° C. for 3 days, cooled to room temperature, and filtered through Celite. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.30) to give the title compound (90.3 mg, 41%) as a solid: PNMR (300 MHz, CDCl3): δ1.20 (d, 6 H, J=6.6 Hz), 1.28 (s, 6 H), 1.38 (t, 3 H, J=7.1 Hz), 1.71 (t, 2 H, J=6.0 Hz), 3.19 (t, 2 H, J=6.0 Hz), 4.02 (sp, 1 H, J=6.6 Hz), 4.34 (q, 2 H, J=7.1 Hz), 5.92 (s, 1 H), 6.43 (dd, 1 H, J=8.1, 2.1 Hz), 6.50 (d, 1 H, J=2.1 Hz), 6.97 (d, 2 H, J=8.7 Hz), 7.14 (d, 1 H, J=8.1 Hz), 7.90 (d, 2 H, J=8.7 Hz). were added cooled to room temperature filtered through Celite The filtrate was concentrated under reduced pressure the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.30)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7-Amino-1-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydroquinoline (Compound 33, 130 mg, 0.5954 mmol) was placed into the round bottom flask charged with argon and Pd2 (dab)3 (1.363 mg, 0.25 mol %), and BINAP (2.78 mg, 0.75 mol %) were added, followed by addition of NaOtBu (80.11 mg, 0.8335 mmol), ethyl iodobenzoate (230 mg, 0.8335 mmol) and toluene (3 mL). The resulting mixture was stirred at 80° C. for 3 days, cooled to room temperature, and filtered through Celite. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.30) to give the title compound (90.3 mg, 41%) as a solid: PNMR (300 MHz, CDCl3): δ1.20 (d, 6 H, J=6.6 Hz), 1.28 (s, 6 H), 1.38 (t, 3 H, J=7.1 Hz), 1.71 (t, 2 H, J=6.0 Hz), 3.19 (t, 2 H, J=6.0 Hz), 4.02 (sp, 1 H, J=6.6 Hz), 4.34 (q, 2 H, J=7.1 Hz), 5.92 (s, 1 H), 6.43 (dd, 1 H, J=8.1, 2.1 Hz), 6.50 (d, 1 H, J=2.1 Hz), 6.97 (d, 2 H, J=8.7 Hz), 7.14 (d, 1 H, J=8.1 Hz), 7.90 (d, 2 H, J=8.7 Hz). were added cooled to room temperature filtered through Celite The filtrate was concentrated under reduced pressure the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.30)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Isopropyl-4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-7-ylamine (Compound 45, 500 mg, 2.152 mmol) was placed into the round bottom flask charged with argon. Pd2 (dab)3 (4.926 mg, 0.25 mol %), and BINAP (10.05 mg, 0.75 mol %) were added, followed by NaOtBu (405.27 mg, 3.012 mmol), ethyl iodobenzoate (831.7 mg, 3.012 mmol) and toluene (8 mL). The resulting mixture was stirred at 80° C. for 3 days, cooled to room temperature, and filtered through Celite. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.26) to give the title compound (642.76 mg, 79%) as a pale yellow solid: charged with argon cooled to room temperature filtered through Celite The filtrate was concentrated under reduced pressure the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.26)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7-Amino-1-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydroquinoline (Compound 33, 130 mg, 0.5954 mmol) was placed into the round bottom flask charged with argon and Pd2 (dab)3 (1.363 mg, 0.25 mol %), and BINAP (2.78 mg, 0.75 mol %) were added, followed by addition of NaOtBu (80.11 mg, 0.8335 mmol), ethyl iodobenzoate (230 mg, 0.8335 mmol) and toluene (3 mL). The resulting mixture was stirred at 80° C. for 3 days, cooled to room temperature, and filtered through Celite. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.30) to give the title compound (90.3 mg, 41%) as a solid: PNMR (300 MHz, CDCl3): δ1.20 (d, 6 H, J=6.6 Hz), 1.28 (s, 6 H), 1.38 (t, 3 H, J=7.1 Hz), 1.71 (t, 2 H, J=6.0 Hz), 3.19 (t, 2 H, J=6.0 Hz), 4.02 (sp, 1 H, J=6.6 Hz), 4.34 (q, 2 H, J=7.1 Hz), 5.92 (s, 1 H), 6.43 (dd, 1 H, J=8.1, 2.1 Hz), 6.50 (d, 1 H, J=2.1 Hz), 6.97 (d, 2 H, J=8.7 Hz), 7.14 (d, 1 H, J=8.1 Hz), 7.90 (d, 2 H, J=8.7 Hz). were added cooled to room temperature filtered through Celite The filtrate was concentrated under reduced pressure the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.30)