Sodium borohydride → HCID 59441716, compound

HRID 1014274Notes

Reaction equation

HRID 1014274 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-])=O)[N:8]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[CH2:7][CH2:6]2.[BH4-].[Na+]>C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[NH2:12])[N:8]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)(=[O:16])=[O:17])[CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59442060HCID 59442060, compound

Product 1

HCID 59441716HCID 59441716, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A yellow slurry of 5-(methyloxy)-1-[(4-methylphenyl)sulfonyl]-6-nitro-2,3-dihydro-1H-indole (16.1 g, 46 mmol) and NiCl2.6H2O (3.29 g, 13.9 mmol) in THF (150 mL) and MeOH (300 mL) was treated with NaBH4 (5.2 g, 139 mmol) in small portions. The resulting mixture was stirred for 1 h, concentrated onto Celite and purified by column chromatography using 0-10% MeOH (containing 0.2% NH3)/CH2Cl2to obtain 5-(methyloxy)-1-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1H-indol-6-amine as white solid (11.94 g, 81%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.33 (s, 3H), 2.63 (t, J=8.15 Hz, 2H), 3.66 (s, 3H), 3.77 (t, J=8.06 Hz 2H), 4.79 (s, 2H), 6.58 (s, 1H), 6.94 (s, 1H), 7.34 (d, J=7.87 Hz, 2H), 7.62 (d, J=7.87 Hz, 2H); ESIMS (M+H)+=320.12.

Workup

  1. concentrationconcentrated onto Celite
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-d5183cb989c647ac9b5a1a0d2945aa0f
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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