3-(Trifluoromethyl)phenyl isocyanate → HCID 58677559, compound

HRID 1012617Notes

Reaction equation

HRID 1012617 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:26])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:12][C:11]=2[Cl:25])=[O:9])[CH:7]=1.[F:27][C:28]([F:39])([F:38])[C:29]1[CH:30]=[C:31]([N:35]=[C:36]=[O:37])[CH:32]=[CH:33][CH:34]=1>N1C=CC=CC=1>[Cl:25][C:11]1[CH:12]=[C:13]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[F:24])[CH:14]=[CH:15][C:10]=1[C:8]([C:6]1[CH:7]=[C:2]([NH:1][C:36]([NH:35][C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([C:28]([F:27])([F:38])[F:39])[CH:30]=2)=[O:37])[CH:3]=[CH:4][C:5]=1[CH3:26])=[O:9]

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 11538012(5-Amino-2-methyl-phenyl)-[2-chloro-4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Product 1

HCID 58677559HCID 58677559, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 494 (0.03 g, 0.08 mmol) was dissolved in pyridine (0.2 mL) and 3-(trifluoromethyl)phenyl isocyanate (0.017 mL, 0.12 mmol) was added. The solution was stirred at room temperature for 1.5 h. Work up as described in the preparation of compound 259. The crude product was purified by flash chromatography using EtOAc/petroleum ether (40-60) 2:3 as the eluent. This afforded the title compound as a slightly coloured solid. 13C NMR (CD3OD) δ 198.3, 161.1 (dd), 157.9 (dd), 155.0, 151.3, 141.5, 141.2, 138.1, 136.2, 135.0, 132.9, 132.8, 132.2 (q), 130.7, 128.8, 127.5 (dd), 126.0 (dd), 125.6 (q), 123.4, 123.0, 121.2, 120.0 (q), 116.6, 116.5 (q), 113.0, 112.6 (dd), 105.8 (dd), 19.7

Workup

  1. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-bc0a3ac51367483faf8a1dedc56f4056
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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