3,5-Difluoroaniline → HCID 11641326, compound

HRID 2067300Notes

Reaction equation

HRID 2067300 reaction equation
FC1C=C(F)C=CC=1NC1C=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[CH3:57])=[O:42])=[C:37]([Cl:58])[CH:36]=1.[F:59][C:60]1[CH:61]=[C:62]([NH2:67])[CH:63]=[C:64]([F:66])[CH:65]=1>>[Cl:58][C:37]1[CH:36]=[C:35]([NH:67][C:62]2[CH:61]=[C:60]([F:59])[CH:65]=[C:64]([F:66])[CH:63]=2)[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[CH3:57])=[O:42]

Participants

4

Reactant 3

HCID 965953,5-DifluoroanilineHCID 11510648HCID 11510648, compoundHCID 69606498HCID 69606498, compound

Product 1

HCID 11641326HCID 11641326, compound

Procedure

The reaction was carried out similarly as described in the preparation of compound 148, using compound 471 (0.13 mmol) and 3,5-difluoro-phenylamine (0.13 mmol). The crude product was purified by flash chromatography using MeOH/DCM 1:20 as the eluent to afford the title compound. 13C NMR (CDCl3) δ 195.0, 163.8 (dd), 146.6, 146.4, 143.1 (t), 140.5, 138.4, 135.2, 134.8, 133.6, 132.7, 132.6, 132.3, 129.4, 122.5, 121.0, 120.1, 118.1, 114.5, 102.2 (m), 98.2 (t), 61.5, 28.8, 20.0

Workup

  1. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-ce77a9a10a3e49349982152346b8b983
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

Loading…