4-Chloro-3-Fluorobenzaldehyde → HCID 86705486, compound

HRID 2279479Notes

Reaction equation

HRID 2279479 reaction equation
O1C(C=O)=CN=C1.[Cl:8]C1C=CC(C=O)=CC=1F.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C@H:25]([NH2:28])[CH2:26][CH3:27])=[CH:21][C:20]=1[F:29].ClC1C=CC(C(N)CC)=CC=1F>>[ClH:8].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C@H:25]([NH2:28])[CH2:26][CH3:27])=[CH:21][C:20]=1[F:29]

Participants

5

Reactant 4

HCID 27249854-Chloro-3-FluorobenzaldehydeHCID 118293725-OXAZOLECARBOXALDEHYDEHCID 55270991HCID 55270991, compoundHCID 86705487HCID 86705487, compound

Product 1

HCID 86705486HCID 86705486, compound

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.

Workup

  1. customThe crude product was purified by SiO2 chromatography
  2. washeluting with DCM/MeOH (500:40)
  3. customto 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)

Sources & evidence

ORD record
ord-71a96584298d4d95aacf36971b7627f4
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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