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

HRID 468350노트

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HRID 468350 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-4a9259042506427482c4800fd79c2d32
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623905B2

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