3,4-Difluoroaniline → HCID 11532445, compound

HRID 2067272Notes

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.[F:59]C1C=C(N)C=CC=1F>>[F:59][C:5]1[CH:4]=[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:2]=[CH:7][C:6]=1[F:8]

Participants

Reactant 3

HCID 774693,4-Difluoroaniline

HCID 11510648HCID 11510648, compound

HCID 68418335HCID 68418335, compound

Product 1

HCID 11532445HCID 11532445, compound

Procedure

The reaction was carried out similarly as described in the preparation of compound 148, using compound 452 (0.13 mmol) and 3,4-difluoro-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, 149.6 (dd), 147.5, 145.7, 144.7 (dd), 142.3, 142.2, 138.4 (dd), 135.3, 135.2, 134.4, 132.1, 127.0, 120.7, 120.5, 118.4, 117.9 (d), 117.7, 116.0 (dd), 111.4, 108.5 (d), 60.2, 29.2, 22.0, 18.9

Workup

customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record: ord-7b6802b958c2409080556eabc15531c9
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293772B2

Reaction notes

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