Sodium cyanoborohydride → tert-butyl 3-({[5-(aminocarbonyl)-1H-imidazol-4-yl]amino}methyl)-4-fluoro-1H-indole-1-carboxylate

HRID 912675ノート

反応式

HRID 912675 の反応式
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:18]=O)=[CH:5][N:6]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].Cl.Cl.[NH:22]1[C:26]([C:27]([NH2:29])=[O:28])=[CH:25][N:24]=[CH:23]1.C([BH3-])#[N:31].[Na+]>CO>[NH2:29][C:27]([C:26]1[NH:22][CH:23]=[N:24][C:25]=1[NH:31][CH2:18][C:4]1[C:3]2[C:7](=[CH:8][CH:9]=[CH:10][C:2]=2[F:1])[N:6]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH:5]=1)=[O:28]

参加物

5

反応物 3

HCID 5003444Sodium cyanoborohydrideHCID 21703850HCID 21703850、化合物HCID 86631123HCID 86631123、化合物

生成物 1

HCID 67417268tert-butyl 3-({[5-(aminocarbonyl)-1H-imidazol-4-yl]amino}methyl)-4-fluoro-1H-indole-1-carboxylate収率 15.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of tert-butyl 4-fluoro-3-formyl-1H-indole-1-carboxylate (1.10 g, 3.0 mmol, obtained from Example 11(a)), 1H-imidazole-5-carboxamide dihydrochloride (0.49 g, 3.0 mmol) and sodium cyanoborohydride (0.38 g, 6.0 mmol) in MeOH (10 mL) was stirred o.n. The reaction mixture was partitioned between H2O (25 mL) and CHCl3 (3×25 mL), the combined organic phase was dried over MgSO4 and evaporated. Purification by flash chromatography using a gradient of MeOH (5-10%) in CHCl3 gave the title compound (0.17 g, 15%). MS (ESI) m/z 374 (M+1).

後処理

  1. customThe reaction mixture was partitioned between H2O (25 mL) and CHCl3 (3×25 mL)
  2. dry with materialthe combined organic phase was dried over MgSO4
  3. customevaporated
  4. customPurification by flash chromatography

出典と根拠

ORDレコード
ord-c34636f04cda45dd93d07272845d5072
出典データセット
uspto-grants-2011_09
特許番号
US08026244B2

反応ノート

読み込み中…