Sodium borohydride → (+/-)-Ethyl (4-amino-3-methyl-2,3-dihydro-1H-indol-3-yl)acetate

HRID 551013Notes

Reaction equation

HRID 551013 reaction equation
[CH3:1][C:2]1([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-])=O)[NH:4][C:3]1=S.[BH4-].[Na+]>CO.C1COCC1.[Ni]>[NH2:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[C:2]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH3:1])[CH2:3][NH:4]2

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 86629730(+/-)-Ethyl (3-methyl-4-nitro-2-thioxo-2,3-dihydro-1H-indol-3-yl)acetate

Product 1

HCID 86629731(+/-)-Ethyl (4-amino-3-methyl-2,3-dihydro-1H-indol-3-yl)acetate

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (±)-ethyl (3-methyl-4-nitro-2-thioxo-2,3-dihydro-1H-indol-3-yl)acetate from Step A (3.65 g, 12.4 mmol) and nickel (H) chloride hexahydrate (23.6 g, 99.2 mmol) in MeOH (30 mL) and THF (30 mL), at 0° C., was added NaBH4 (11.3 g, 298 mmol) in portions, over 1 h. The resulting mixture was stirred for 10 min, then filtered through a pad of Celite, washing with MeOH, and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with CH2Cl2:MeOH—90:10, to give the title compound. MS: m/z=235 (M+1).

Workup

  1. filtrationfiltered through a pad of Celite
  2. washwashing with MeOH
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-dd305d2ae2554f3c8ef45fa57a4dae51
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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