2,5-Difluoroaniline → HCID 11511108, compound

HRID 2067299Notes

Reaction equation

HRID 2067299 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:65]=[CH:64][C:63]([F:66])=[CH:62][C:61]=1[NH2:67]>>[Cl:58][C:37]1[CH:36]=[C:35]([NH:67][C:61]2[CH:62]=[C:63]([F:66])[CH:64]=[CH:65][C:60]=2[F:59])[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 677752,5-DifluoroanilineHCID 11510648HCID 11510648, compoundHCID 69606498HCID 69606498, compound

Product 1

HCID 11511108HCID 11511108, compound

Procedure

The reaction was carried out similarly as described in the preparation of compound 148, using compound 471 (0.13 mmol) and 2,5-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 194.9, 158.8 (d), 150.2 (d), 146.3 (d), 140.4, 138.4, 135.2, 134.8, 133.5, 132.7, 129.9, 122.5, 121.0, 119.9, 117.9, 116.6 (dd), 114.5, 109.5 (dd), 107.1 (d), 61.6, 28.7, 20.1

Workup

  1. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-a1777b006f204090a28c260bd079e75a
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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