Sodium borohydride → HCID 21071461, compound

HRID 1666801Notes

Reaction equation

HRID 1666801 reaction equation
[N+:1]([CH:4]=[CH:5][C:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:12][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][C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:12][CH:13]=2)[NH:8][CH:7]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 674434643-(2-Nitrovinyl)-6-ethoxycarbonyl-1H-indole

Product 1

HCID 21071461HCID 21071461, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Combine 3-(2-nitrovinyl)-6-ethoxycarbonyl-1H-indole (4.0 g, 15.37 mmol) and NaBH4 (726.7 mg, 19.21 mmol) in 100 ml of THF/Methanol (9:1) and stir at ambient temperature. After 1.5 hours, concentrate to residue. Partition the residue between brine and ethyl acetate, wash with brine, combine the organic layers, dry (Na2SO4), then evaporate to give the title compound as a yellow powder: mp 124-127° C. MS (ACPI): m/e 263.0 (M+1). Analysis for C13H14N2O4: Calcd: C, 59.54; H, 5.38; N, 10.68. found: C, 59.40; H, 5.36; N, 10.53.

Workup

  1. concentrationconcentrate to residue
  2. customPartition the residue between brine and ethyl acetate
  3. washwash with brine
  4. dry with materialdry (Na2SO4)
  5. customevaporate

Sources & evidence

ORD record
ord-450ae7967b794a448970e62a4ffa5917
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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