Hydroxylamine → 3-(4-fluoro-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid hydroxyamide

HRID 1395898

反応式

HRID 1395898 の反応式
[OH-:1].[Na+].[NH2:3]O.C[O:6][C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[C:12]2[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)=O>C1COCC1.CO.O>[OH:1][NH:3][C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[C:12]2[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)=[O:6]

参加物

6

反応物 3

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 694495523-(4-fluoro-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester

生成物 1

HCID 247539023-(4-fluoro-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid hydroxyamide収率 50%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

To a solution of sodium hydroxide (64 mg, 1.6 mmol) and 50% aqueous hydroxylamine (0.65 mL) was added 3-(4-fluoro-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester (58 mg, 0.2 mmol) dissolved in THF/MeOH (1 mL, 1:1). After stirring 4 hr at room temperature, the solution was diluted with water (4 mL) and the volatile solvents were removed in vacuo. The solution was then neutralized to pH=7-8 with 1N HCl and then subjected to HPLC purification to provide 3-(4-fluoro-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid hydroxyamide (32 mg, 50% yield). 1H NMR (400 MHz, DMSO) δ 11.05 (s, 1H), 8.83 (br s, 1H), 7.97 (s, 1H), 7.57 (dd, 1H, J=1.7, 8.6 Hz), 7.41 (d, 1H, J=8.6 Hz) 7.30 (m, 2H), 7.18 (s, 1H), 7.08 (m, 2H), 4.03 (s, 2H), 3.74 (s, 3H).

後処理

  1. customthe volatile solvents were removed in vacuo
  2. customsubjected to HPLC purification

出典と根拠

ORDレコード
ord-143a18fdbc884efd951bc5a877438654
出典データセット
uspto-grants-2014_12
特許番号
US08900565B2

関連ノート

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