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

HRID 2037964Notes

Reaction equation

HRID 2037964 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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, 1 H), 7.06 (d, J=2.4 Hz, 1 H), 6.84 (d, J=2.4 Hz, 1 H), 6.14 (d, J=2.4 Hz, 1 H), 3.57 (br s, 2 H), 1.38 (s, 9 H). MS (ESI) m/z: 214 (M+H+).

Workup

  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)

Sources & evidence

ORD record
ord-12ca9806f7164109b0f5f49cbdc80e19
Source dataset
uspto-grants-2013_11
Patent number
US08575209B2

Reaction notes

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