3-Chloro-4-fluoroaniline → HCID 11655645, compound

HRID 2067267Notes

Reaction equation

F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[CH:23]=[C:22]([N:24]3[CH:28]=[C:27]([CH2:29][CH2:30][OH:31])[N:26]=[N:25]3)[CH:21]=[CH:20][C:19]=2[CH3:32])=[O:17])=[C:12]([CH3:33])[CH:11]=1.BrC1C=CC(C(C2C=C(N3C=C(CCO)N=N3)C=CC=2C)=O)=C(C)C=1.[Cl:59]C1C=C(N)C=CC=1F>>[Cl:59][C:7]1[CH:2]=[C:3]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([C:18]3[CH:23]=[C:22]([N:24]4[CH:28]=[C:27]([CH2:29][CH2:30][OH:31])[N:26]=[N:25]4)[CH:21]=[CH:20][C:19]=3[CH3:32])=[O:17])=[C:12]([CH3:33])[CH:11]=2)[CH:4]=[CH:5][C:6]=1[F:8]

Participants

Reactant 3

HCID 97083-Chloro-4-fluoroaniline

HCID 11510648HCID 11510648, compound

HCID 68418335HCID 68418335, compound

Product 1

HCID 11655645HCID 11655645, compound

Procedure

The reaction was carried out similarly as described in the preparation of compound 148, using compound 452 (0.13 mmol) and 3-chloro-4-fluoro-phenylamine (0.13 mmol). The crude product was purified by continuous gradient flash chromatography using MeOH/DCM/petroleum ether (40-60) 0:50:50, 0:100:0 and 5:95:0 as the eluent to afford the title compound as yellow solid. 13C NMR (DMSO-d6) δ 196.4, 152.6 (d), 147.6, 145.8, 142.3, 142.3, 138.6 (d), 135.3 (d), 134.4, 132.2, 126.9, 121.1, 120.7, 120.5, 120.0 (d), 119.9 (d), 118.4, 117.7, 117.5 (d), 111.3, 60.2, 29.2, 22.0, 18.9

Workup

customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record: ord-5a329ee5d8a143e090d5672e8b58ad77
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293772B2

Reaction notes

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