Sodium borohydride → 5-amino-2-tert-butyl-1H-indole-7-carbonitrile

HRID 503345ノート

反応式

HRID 503345 の反応式
[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([N+:14]([O-])=O)=[CH:9][C:8]=2[C:17]#[N:18])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[NH2:14][C:10]1[CH:11]=[C:12]2[C:7](=[C:8]([C:17]#[N:18])[CH:9]=1)[NH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:13]2

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 534211842-Tert-butyl-5-nitro-1H-indole-7-carbonitrile

生成物 1

HCID 591292165-amino-2-tert-butyl-1H-indole-7-carbonitrile収率 61.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of crude product 2-tert-butyl-5-nitro-1H-indole-7-carbonitrile (0.87 g, 3.6 mmol) in MeOH (10 mL) was added NiCl2.6H2O (1.8 g, 7.2 mmol) at −5° C. The reaction mixture was stirred for 30 min, then NaBH4 (0.48 g, 14.32 mmol) was added to the reaction mixture at 0° C. After 5 min, the reaction mixture was quenched with water, filtered and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated under vacuum to obtain the crude product, which was purified by column chromatography (5-20% EtOAc in petroleum ether) to obtain 5-amino-2-tert-butyl-1H-indol-7-carbonitrile (470 mg, 32% over two steps). 1H NMR (400 MHz, CDCl3) δ 8.25 (s, 1H), 7.06 (d, J=2.4 Hz, 1H), 6.84 (d, J=2.4 Hz, 1H), 6.14 (d, J=2.4 Hz, 1H), 3.57 (br s, 2H), 1.38 (s, 9H). MS (ESI) m/z: 214 (M+H+).

後処理

  1. waitAfter 5 min
  2. customthe reaction mixture was quenched with water
  3. filtrationfiltered
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customto obtain the crude product, which
  8. customwas purified by column chromatography (5-20% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-2fe8e75f7d1547d4b6afc6958e003128
出典データセット
uspto-grants-2010_08
特許番号
US07776905B2

反応ノート

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