Methyl iodide → HCID 59375061、化合物

HRID 1811129ノート

反応式

HRID 1811129 の反応式
[C:1](=O)([O-])[O-].[K+].[K+].IC.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[C:28]2[C:27]3[C:22](=[CH:23][C:24]([OH:29])=[CH:25][CH:26]=3)[NH:21][C:20]=2[C:19]([C:30]([NH2:32])=[O:31])=[CH:18][CH:17]=1>CS(C)=O.CCOC(C)=O>[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[C:28]2[C:27]3[C:22](=[CH:23][C:24]([O:29][CH3:1])=[CH:25][CH:26]=3)[NH:21][C:20]=2[C:19]([C:30]([NH2:32])=[O:31])=[CH:18][CH:17]=1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59375146HCID 59375146、化合物

生成物 1

HCID 59375061HCID 59375061、化合物収率 9.3%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Potassium carbonate (25.1 mg, 0.182 mmol) and iodomethane (4.9 mL, 0.079 mmol) were added to a solution of 4-(2-fluorophenyl)-7-hydroxy-9H-carbazole-1-carboxamide (Example 40-1, 19.4 mg, 0.061 mmol) in DMSO (1 mL) and the mixture was stirred at rt. After 17 h, the mixture was diluted with EtOAc (30 mL), washed with saturated aqueous ammonium chloride (5 mL), water (2×5 mL), and brine (5 mL), dried and concentrated. The residue was purified by preparative HPLC to provide 4-(2-fluorophenyl)-7-methoxy-9H-carbazole-1-carboxamide (1.9 mg, 9%). 1H NMR (400 MHz, chloroform-d) δ 10.39 (1 H, br. s.), 7.58 (1 H, d, J=7.70 Hz), 7.44-7.55 (2 H, m), 7.28-7.39 (2 H, m), 7.07-7.22 (2 H, m), 7.00 (1 H, d, J=2.20 Hz), 6.65 (1 H, dd, J=8.80, 2.42 Hz), 6.57 (2 H, br. s.), 3.88 (3 H, s). Mass spectrum m/z 335.0 (M+H)+.

後処理

  1. washwashed with saturated aqueous ammonium chloride (5 mL), water (2×5 mL), and brine (5 mL)
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-8f16241c0857419e9b86d019ff1eef0b
出典データセット
uspto-grants-2013_01
特許番号
US08362065B2

反応ノート

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