2-Bromo-1-[2-(trifluoromethyl)phenyl]ethan-1-one → 2'-Nitro-4-[4-(2-trifluoromethyl-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid

HRID 1519263ノート

反応式

HRID 1519263 の反応式
C[O:2][C:3]([C:5]1[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])=[CH:7][CH:8]=[C:9]([C:11](=[S:13])[NH2:12])[CH:10]=1)=[O:4].[F:23][C:24]([F:36])([F:35])[C:25]1[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=1[C:27](=O)[CH2:28]Br>O>[N+:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:6]1[C:5]([C:3]([OH:2])=[O:4])=[CH:10][C:9]([C:11]2[S:13][CH:28]=[C:27]([C:26]3[CH:31]=[CH:32][CH:33]=[CH:34][C:25]=3[C:24]([F:23])([F:35])[F:36])[N:12]=2)=[CH:8][CH:7]=1)([O-:22])=[O:21]

参加物

4

反応物 2

HCID 27784302-Bromo-1-[2-(trifluoromethyl)phenyl]ethan-1-oneHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2 回

生成物 1

HCID 715360812'-Nitro-4-[4-(2-trifluoromethyl-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid収率 19%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

2′-Nitro-4-[4-(2-trifluoromethyl-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (56 mg, 19%) was prepared from 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4) and 2-(trifluoromethyl)phenacyl bromide (available from Maybridge) using the procedure described for the preparation of Example 18 except that the entire 4 mL of water was added at the beginning of the hydrolysis step rather than being added in two portions. 1H NMR (300 MHz, DMSO-d6) δ 13.06 (br s, 1H), 8.52 (d, J=1.6 Hz, 1H), 8.20 (dd, J=8.2, 1.7 Hz, 1H), 8.13 (d, J=8.0 Hz, 1H), 7.96 (s, 1H), 7.88 (d, J=7.6 Hz, 1H), 7.64-7.80 (m, 4H), 7.40-7.46 (m, 2H).

後処理

  1. additionwas added at the beginning of the hydrolysis step rather
  2. additionthan being added in two portions

出典と根拠

ORDレコード
ord-0a9dac9aa13b48f2ae465154911f2658
出典データセット
uspto-grants-2015_07
特許番号
US09073881B2

反応ノート

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