Sodium cyanoborohydride → 1-(5-Chloro-2-methoxyphenyl)-3-indolin-4-yl-urea

HRID 240470Notes

Reaction equation

HRID 240470 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH3:22])=[C:6]([NH:8][C:9]([NH:11][C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[CH:14]=[CH:15][NH:16]3)=[O:10])[CH:7]=1.[BH3-]C#N.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH3:22])=[C:6]([NH:8][C:9]([NH:11][C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[CH2:14][CH2:15][NH:16]3)=[O:10])[CH:7]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 666135101-(5-chloro-2-methoxyphenyl)-3-(1H-indol-4-yl)urea

Product 1

HCID 666116261-(5-Chloro-2-methoxyphenyl)-3-indolin-4-yl-ureaYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 1-(5-chloro-2-methoxyphenyl)-3-(1H-indol-4-yl)urea (6.3 g, 20 mmol) in acetic acid (50 mL) was added portionwise NaBH3CN (1.9 g, 30 mmol), and the resulting mixture was stirred at rt for 1 h. The solvent was evaporated and residue was diluted with water, neutralized with NaHCO3 and extracted with EtOAc. The combined organic phase were washed with brine, dried and evaporated to give crude 1-(5-chloro-2-methoxyphenyl)-3-(2,3-dihydro-1H-indol-4-yl)urea (6.3 g, 100%), which was used directly in the next step without purification.

Workup

  1. customThe solvent was evaporated
  2. additionresidue was diluted with water
  3. extractionextracted with EtOAc
  4. washThe combined organic phase were washed with brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-d53227b0993a4ea985965ad17b8dd766
Source dataset
uspto-grants-2014_02
Patent number
US08648086B2

Reaction notes

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