Sodium borohydride → HCID 21071457, compound

HRID 1666845Notes

Reaction equation

HRID 1666845 reaction equation
[N+:1]([CH:4]=[CH:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[NH:8][CH:7]=1)([O-:3])=[O:2].[BH4-].[Na+]>C1COCC1.CO>[N+:1]([CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[NH:8][CH:7]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 67444276HCID 67444276, compound

Product 1

HCID 21071457HCID 21071457, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Treat a solution of 3-(2-nitrovinyl)-5-methoxycarbonyl-1H-indole (57 mg, 0.23 mmol) in 9 mL THF and 2 mL MeOH with NaBH4 (26 mg 0.69 mmol). Stir at ambient temperature overnight, concentrate to dryness and partition between conc. NH4OH (10 mL) and dichloromethane. Extract the aqueous layer with dichloromethane, acidify with cone. HCl and extract twice with dichloromethane. Combine the organic layers, concentrate, and chromatograph on silica gel eluting with 1% MeOH in CHCl3 to give the title compound as a solid: 1H NMR (CDCl3) 8.35 (bs, 1H), 8.32 (s, 1H), 7.92-7.90 (m, 1H), 7.38-7.36 (d, 1H), 7.12-7.11 (m, 1H), 4.69-4.65 (t, 2H), 3.93 (s, 3H), 3.51-3.48 (t, 2H); ISMS 248 (M+).

Workup

  1. concentrationconcentrate to dryness
  2. custompartition between conc. NH4OH (10 mL) and dichloromethane
  3. extractionExtract the aqueous layer with dichloromethane
  4. extractionHCl and extract twice with dichloromethane
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-7ac5d6a6d6d1400bacc922de67676cf2
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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