2,4-Difluoroaniline → HCID 11547651, compound

HRID 2067279Notes

Reaction equation

HRID 2067279 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9]C1C=CC(C(C2C=C(N3C=C(CCO)N=N3)C=CC=2C)=O)=C(C)C=1.Br[C:35]1[CH:40]=[CH:39][C:38]([C:41]([C:43]2[CH:48]=[C:47]([N:49]3[CH:53]=[C:52]([CH2:54][CH2:55][OH:56])[N:51]=[N:50]3)[CH:46]=[CH:45][C:44]=2[Cl:57])=[O:42])=[C:37]([Cl:58])[CH:36]=1.FC1C=C(F)C=CC=1N>>[Cl:58][C:37]1[CH:36]=[C:35]([NH:9][C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH:40]=[CH:39][C:38]=1[C:41]([C:43]1[CH:48]=[C:47]([N:49]2[CH:53]=[C:52]([CH2:54][CH2:55][OH:56])[N:51]=[N:50]2)[CH:46]=[CH:45][C:44]=1[Cl:57])=[O:42]

Participants

4

Reactant 3

HCID 97092,4-DifluoroanilineHCID 11510648HCID 11510648, compoundHCID 68420453HCID 68420453, compound

Product 1

HCID 11547651HCID 11547651, compound

Procedure

The reaction was carried out similarly as described in the preparation of compound 148, using compound 456 (0.91 mmol) and 2,4-difluoro-phenylamine (0.91 mmol). The crude product was purified by continuous gradient flash chromatography using MeOH/DCM 0:100, 10:90 as the eluent to afford the title compound as yellow solid. 13C NMR (CDCl3) δ 191.1, 159.6 (dd), 155.9 (dd), 149.1, 146.7, 141.1, 136.1, 135.7, 134.5, 131.7, 131.6, 126.9, 125.1 (dd), 123.8 (dd), 122.8, 121.0, 119.9, 116.1, 112.8, 111.7 (dd), 105.1 (dd), 61.5, 28.7

Workup

  1. customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record
ord-8381310c5154469f984e5fffd75e956d
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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