2-cyclopropyloxyethanol

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

Procedure: To a solution of 2-cyclopropoxyethanol (400 mg, 3.92 mmol) in DCM (10 mL) were added TsCl (821 mg, 4.31 mmol) and Et3N (0.6 mL, 4.31 mmol). The reaction was stirred at room temperature overnight. Then, 1N HCl was added, and the reaction was extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give a yellow oil. The oil was purified by preparative TLC to obtain intermediate BP (50 mg) as a yellow oil. the reaction was extracted with DCM The combined organic layers were washed with brine dried over Na2SO4 concentrated to give a yellow oil The oil was purified by preparative TLC to obtain intermediate BP (50 mg) as a yellow oil

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

Procedure: This compound was prepared from 2,5,6-trichloronicotinamide, 2-cyclopropoxyethanol, and benzo[c][1,2]oxaborole-1,5(3H)-diol in a similar manner to that of D230. 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 0.35-0.4 (m, 4H), 3.2-3.32 (m, 1H), 3.55-3.62 (m, 3H), 4.1-4.12 (m, 2H), 5.0 (s, 2H), 7.24 (dd, J=6.0, 1.4 Hz, 1H), 7.33 (s, 1H), 7.8 (d, J=6.7 Hz, 1H), 8.6 (s, 1H), 9.26 (s, 1H).

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

Procedure: To a solution of 2-cyclopropoxyethanol (400 mg, 3.92 mmol) in DCM (10 mL) were added TsCl (821 mg, 4.31 mmol) and Et3N (0.6 mL, 4.31 mmol). The reaction was stirred at room temperature overnight. Then, 1N HCl was added, and the reaction was extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give a yellow oil. The oil was purified by preparative TLC to obtain intermediate BP (50 mg) as a yellow oil. the reaction was extracted with DCM The combined organic layers were washed with brine dried over Na2SO4 concentrated to give a yellow oil The oil was purified by preparative TLC to obtain intermediate BP (50 mg) as a yellow oil

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

Procedure: To a solution of 2-cyclopropoxyethanol (400 mg, 3.92 mmol) in DCM (10 mL) were added TsCl (821 mg, 4.31 mmol) and Et3N (0.6 mL, 4.31 mmol). The reaction was stirred at room temperature overnight. Then, 1N HCl was added, and the reaction was extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give a yellow oil. The oil was purified by preparative TLC to obtain intermediate BP (50 mg) as a yellow oil. the reaction was extracted with DCM The combined organic layers were washed with brine dried over Na2SO4 concentrated to give a yellow oil The oil was purified by preparative TLC to obtain intermediate BP (50 mg) as a yellow oil

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

Procedure: To a solution of 2-cyclopropoxyethanol (400 mg, 3.92 mmol) DCM (10 mL) were added TsCl (821 mg, 4.31 mmol) and Et3N (0.6 mL, 4.31 mmol). The reaction was stirred at room temperature overnight. Then, 1N HCl was added, and the reaction was extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give a yellow oil. The oil was purified by preparative TLC to obtain intermediate BP (50 mg) as a yellow oil. the reaction was extracted with DCM The combined organic layers were washed with brine dried over Na2SO4 concentrated to give a yellow oil The oil was purified by preparative TLC to obtain intermediate BP (50 mg) as a yellow oil

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

Procedure: To a solution of 2-cyclopropoxyethanol (400 mg, 3.92 mmol) DCM (10 mL) were added TsCl (821 mg, 4.31 mmol) and Et3N (0.6 mL, 4.31 mmol). The reaction was stirred at room temperature overnight. Then, 1N HCl was added, and the reaction was extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give a yellow oil. The oil was purified by preparative TLC to obtain intermediate BP (50 mg) as a yellow oil. the reaction was extracted with DCM The combined organic layers were washed with brine dried over Na2SO4 concentrated to give a yellow oil The oil was purified by preparative TLC to obtain intermediate BP (50 mg) as a yellow oil

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

Procedure: This compound was prepared from 2,5,6-trichloronicotinamide, 2-cyclopropoxyethanol, and benzo[c][1,2]oxaborole-1,5(3H)-diol in a similar manner to that of D230. 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 0.35-0.4 (m, 4H), 3.2-3.32 (m, 1H), 3.55-3.62 (m, 3H), 4.1-4.12 (m, 2H), 5.0 (s, 2H), 7.24 (dd, J=6.0, 1.4 Hz, 1H), 7.33 (s, 1H), 7.8 (d, J=6.7 Hz, 1H), 8.6 (s, 1H), 9.26 (s, 1H).

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

Procedure: This compound was prepared from 2,5,6-trichloronicotinamide, 2-cyclopropoxyethanol, and benzo[c][1,2]oxaborole-1,5(3H)-diol in a similar manner to that of D230. 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 0.35-0.4 (m, 4H), 3.2-3.32 (m, 1H), 3.55-3.62 (m, 3H), 4.1-4.12 (m, 2H), 5.0 (s, 2H), 7.24 (dd, J=6.0, 1.4 Hz, 1H), 7.33 (s, 1H), 7.8 (d, J=6.7 Hz, 1H), 8.6 (s, 1H), 9.26 (s, 1H).

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

Procedure: To a solution of 2-cyclopropoxyethanol (400 mg, 3.92 mmol) in DCM (10 mL) were added TsCl (821 mg, 4.31 mmol) and Et3N (0.6 mL, 4.31 mmol). The reaction was stirred at room temperature overnight. Then, 1N HCl was added, and the reaction was extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give a yellow oil. The oil was purified by preparative TLC to obtain intermediate BP (50 mg) as a yellow oil. the reaction was extracted with DCM The combined organic layers were washed with brine dried over Na2SO4 concentrated to give a yellow oil The oil was purified by preparative TLC to obtain intermediate BP (50 mg) as a yellow oil

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

Procedure: To a solution of 2-cyclopropoxyethanol (400 mg, 3.92 mmol) in DCM (10 mL) were added TsCl (821 mg, 4.31 mmol) and Et3N (0.6 mL, 4.31 mmol). The reaction was stirred at room temperature overnight. Then, 1N HCl was added, and the reaction was extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give a yellow oil. The oil was purified by preparative TLC to obtain intermediate BP (50 mg) as a yellow oil. the reaction was extracted with DCM The combined organic layers were washed with brine dried over Na2SO4 concentrated to give a yellow oil The oil was purified by preparative TLC to obtain intermediate BP (50 mg) as a yellow oil

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

Procedure: This compound was prepared from 2,5,6-trichloronicotinamide, 2-cyclopropoxyethanol, and benzo[c][1,2]oxaborole-1,5(3H)-diol in a similar manner to that of D230. 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 0.35-0.4 (m, 4H), 3.2-3.32 (m, 1H), 3.55-3.62 (m, 3H), 4.1-4.12 (m, 2H), 5.0 (s, 2H), 7.24 (dd, J=6.0, 1.4 Hz, 1H), 7.33 (s, 1H), 7.8 (d, J=6.7 Hz, 1H), 8.6 (s, 1H), 9.26 (s, 1H).

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

Procedure: To a solution of 2-cyclopropoxyethanol (400 mg, 3.92 mmol) in DCM (10 mL) were added TsCl (821 mg, 4.31 mmol) and Et3N (0.6 mL, 4.31 mmol). The reaction was stirred at room temperature overnight. Then, 1N HCl was added, and the reaction was extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give a yellow oil. The oil was purified by preparative TLC to obtain intermediate BP (50 mg) as a yellow oil. the reaction was extracted with DCM The combined organic layers were washed with brine dried over Na2SO4 concentrated to give a yellow oil The oil was purified by preparative TLC to obtain intermediate BP (50 mg) as a yellow oil