Methyl iodide → HCID 59375061, 화합물

HRID 1811129노트

반응식

HRID 1811129 반응식
[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

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59375146HCID 59375146, 화합물

생성물 1

HCID 59375061HCID 59375061, 화합물수율 9.3%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-8f16241c0857419e9b86d019ff1eef0b
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362065B2

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