Sodium borohydride → HCID 21071457, compound

HRID 1371908Notes

Reaction equation

HRID 1371908 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 conc. 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. extractionextract twice with dichloromethane
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-9228dcb3f133468baf962134de373fb1
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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