4-Fluoro-3-nitrophenyl isocyanate → 1-[3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(4-fluoro-3-nitro-phenyl)urea

HRID 919414

反応式

HRID 919414 の反応式
[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH2:16])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[O:26])=[CH:20][C:19]=1[N+:27]([O-:29])=[O:28]>C(Cl)Cl>[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH:16][C:25]([NH:24][C:21]2[CH:22]=[CH:23][C:18]([F:17])=[C:19]([N+:27]([O-:29])=[O:28])[CH:20]=2)=[O:26])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

参加物

4

反応物 2

HCID 1441174-Fluoro-3-nitrophenyl isocyanateHCID 115727413-(4-Bromo-1-methyl-1H-pyrazol-5-yl)-4-methoxyaniline

生成物 1

HCID 116912031-[3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(4-fluoro-3-nitro-phenyl)urea収率 69.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine (0.037 g, 0.13 mmol) was treated with 4-fluoro-3-nitrophenyl isocyanate (0.025 g, 0.14 mmol, 1.05 equiv.) in CH2Cl2 (1 mL), in a similar manner as described in Example 1.2 to afford Compound 16 (0.042 g, 0.09 mmol, 69%) as a yellow solid. LCMS m/z (%)=464 (M+H79Br, 100), 466 (M+H81Br, 96). 1H NMR (400 MHz, acetone-d6) δ: 8.55 (s, 1H), 8.44-8.50 (m, 1H), 8.29 (s, 1H), 7.77-7.83 (s, 1H), 7.70 (dd, J=2.7, 9.0 Hz, 1H), 7.49 (s, 1H), 7.37-7.46 (m, 2H), 7.16 (d, J=8.9 Hz, 1H), 3.83 (s, 3H), 3.69 (s, 3H).

出典と根拠

ORDレコード
ord-25d8cc198b3b4887b1d49cdd35ae2f10
出典データセット
uspto-grants-2016_03
特許番号
US09273035B2

関連ノート

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