Water → HCID 23246471, compound

HRID 1884408Notes

Reaction equation

HRID 1884408 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.[BH3-]C#N.[Na+].O>C(O)(=O)C>[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][NH:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 12139076HCID 12139076, compound

Product 1

HCID 23246471HCID 23246471, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-methoxy-5-methylindole 27 (0.48 g, 2.98 mmol) in acetic acid (20 ml) was added NaBH3CN (0.75 g, 9 mmol) portionwise over 10 min (exothermic reaction) and the mixture was then stirred at rt for 0.5 h. Water (2-3 ml) was added and the solvent removed in vacuo. The residue was dissolved in EtOAc and washed with saturated aq. NaHCO3 and brine, dried and evaporated to give 28 as a viscous oil (449 mg, 92%) which was immediately used in the next step; δH (90 MHZ) 6.80 (1 H, d, J 9, 7-H), 6.31 (1 H, d, 6-H), 3.76 (3 H, s, OMe), 3.56 (2 H, t, J 8, 2-H), 3.12 (3 H, t, 3-H) and 2.14 (3 H, s, Me).

Workup

  1. custom(exothermic reaction)
  2. customthe solvent removed in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with saturated aq. NaHCO3 and brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-090374bebb5a4c1092346c93ac7881ef
Source dataset
uspto-grants-2004_07
Patent number
US06765014B1

Reaction notes

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