1-(4-chloro-3-fluorophenyl)propan-1-amine

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

Procedure: (R)-1-(4-chloro-3-fluorophenyl)propan-1-amine hydrochloride (139) was prepared in accord with procedures described in steps 1 and 2 of example 1, except in step 1, oxazole-5-carbaldehyde was replaced with 4-chloro-3-fluorobenzaldehyde. Condensation of (R)-1-(4-chloro-3-fluorophenyl)propan-1-amine and 138 was carried out in accord with step 6 of example 1 except 28 was replaced with 138 and 22 was replaced with 1-(4-chloro-3-fluorophenyl)propan-1-amine. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:40) to afford 0.30 g (75%) of I-38: 1H NMR (400 MHz, d6-DMSO) δ 8.06 (s, 1H), 7.51-7.47 (t, 1H), 7.34 (d, 1H), 7.17 (d, 1H), 6.95 (d, 1H), 6.53 (d, 1H), 4.64-4.55 (m, 2H), 4.38-4.26 (m, 2H), 3.93-3.90 (m, 1H), 3.59-3.55 (m, 2H), 3.46-3.31 (m, 1H), 3.29-3.24 (m, 1H), 2.55-2.50 (m, 2H), 1.76-1.63 (m, 1H), 1.08 (d, 3H), 0.84 (t, 3H); MS m/z (APCI-pos) M+1=422. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:40) to afford 0.30 g (75%) of I-38: 1H NMR (400 MHz, d6-DMSO) δ 8.06 (s, 1H), 7.51-7.47 (t, 1H), 7.34 (d, 1H), 7.17 (d, 1H), 6.95 (d, 1H), 6.53 (d, 1H), 4.64-4.55 (m, 2H), 4.38-4.26 (m, 2H), 3.93-3.90 (m, 1H), 3.59-3.55 (m, 2H), 3.46-3.31 (m, 1H), 3.29-3.24 (m, 1H), 2.55-2.50 (m, 2H), 1.76-1.63 (m, 1H), 1.08 (d, 3H), 0.84 (t, 3H)

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

Procedure: (R)-1-(4-chloro-3-fluorophenyl)propan-1-amine hydrochloride (139) was prepared in accord with procedures described in steps 1 and 2 of example 1, except in step 1, oxazole-5-carbaldehyde was replaced with 4-chloro-3-fluorobenzaldehyde. Condensation of (R)-1-(4-chloro-3-fluorophenyl)propan-1-amine and 138 was carried out in accord with step 6 of example 1 except 28 was replaced with 138 and 22 was replaced with 1-(4-chloro-3-fluorophenyl)propan-1-amine. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:40) to afford 0.30 g (75%) of I-38: 1H NMR (400 MHz, d6-DMSO) δ 8.06 (s, 1H), 7.51-7.47 (t, 1H), 7.34 (d, 1H), 7.17 (d, 1H), 6.95 (d, 1H), 6.53 (d, 1H), 4.64-4.55 (m, 2H), 4.38-4.26 (m, 2H), 3.93-3.90 (m, 1H), 3.59-3.55 (m, 2H), 3.46-3.31 (m, 1H), 3.29-3.24 (m, 1H), 2.55-2.50 (m, 2H), 1.76-1.63 (m, 1H), 1.08 (d, 3H), 0.84 (t, 3H); MS m/z (APCI-pos) M+1=422. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:40) to afford 0.30 g (75%) of I-38: 1H NMR (400 MHz, d6-DMSO) δ 8.06 (s, 1H), 7.51-7.47 (t, 1H), 7.34 (d, 1H), 7.17 (d, 1H), 6.95 (d, 1H), 6.53 (d, 1H), 4.64-4.55 (m, 2H), 4.38-4.26 (m, 2H), 3.93-3.90 (m, 1H), 3.59-3.55 (m, 2H), 3.46-3.31 (m, 1H), 3.29-3.24 (m, 1H), 2.55-2.50 (m, 2H), 1.76-1.63 (m, 1H), 1.08 (d, 3H), 0.84 (t, 3H)

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

Procedure: (R)-1-(4-chloro-3-fluorophenyl)propan-1-amine hydrochloride (139) was prepared in accord with procedures described in steps 1 and 2 of example 1, except in step 1, oxazole-5-carbaldehyde was replaced with 4-chloro-3-fluorobenzaldehyde. Condensation of (R)-1-(4-chloro-3-fluorophenyl)propan-1-amine and 138 was carried out in accord with step 6 of example 1 except 28 was replaced with 138 and 22 was replaced with 1-(4-chloro-3-fluorophenyl)propan-1-amine. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:40) to afford 0.30 g (75%) of I-38: 1H NMR (400 MHz, d6-DMSO) δ 8.06 (s, 1H), 7.51-7.47 (t, 1H), 7.34 (d, 1H), 7.17 (d, 1H), 6.95 (d, 1H), 6.53 (d, 1H), 4.64-4.55 (m, 2H), 4.38-4.26 (m, 2H), 3.93-3.90 (m, 1H), 3.59-3.55 (m, 2H), 3.46-3.31 (m, 1H), 3.29-3.24 (m, 1H), 2.55-2.50 (m, 2H), 1.76-1.63 (m, 1H), 1.08 (d, 3H), 0.84 (t, 3H); MS m/z (APCI-pos) M+1=422. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:40) to afford 0.30 g (75%) of I-38: 1H NMR (400 MHz, d6-DMSO) δ 8.06 (s, 1H), 7.51-7.47 (t, 1H), 7.34 (d, 1H), 7.17 (d, 1H), 6.95 (d, 1H), 6.53 (d, 1H), 4.64-4.55 (m, 2H), 4.38-4.26 (m, 2H), 3.93-3.90 (m, 1H), 3.59-3.55 (m, 2H), 3.46-3.31 (m, 1H), 3.29-3.24 (m, 1H), 2.55-2.50 (m, 2H), 1.76-1.63 (m, 1H), 1.08 (d, 3H), 0.84 (t, 3H)