Potassium Hydroxide → 7-Bromo-4-fluoroindoline

HRID 656072Notes

Reaction equation

HRID 656072 reaction equation
[BH3-]C#N.[Na+].[Br:5][C:6]1[CH:7]=[CH:8][C:9]([F:15])=[C:10]2[C:14]=1[NH:13][CH:12]=[CH:11]2.[OH-].[K+].C([O-])(O)=O.[Na+]>C(O)(=O)C.CCOC(C)=O>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([F:15])=[C:10]2[C:14]=1[NH:13][CH2:12][CH2:11]2

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 43429567-bromo-4-fluoro-1H-indoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 593325897-Bromo-4-fluoroindoline

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaCNBH3 (2.4 g, 38.2 mmol) was added portionwise to a solution of 7-bromo-4-fluoro-1H-indole (1 g, 4.7 mmol) in acetic acid at −10° C. (bath temp). The reaction was stirred overnight, cooled to 0° C. (bath temp), and solid KOH was added. Saturated NaHCO3 and EtOAc were added, the layers were separated, and the organic layer evaporated. The crude product was purified by flash chromatography, giving the title compound.

Workup

  1. additionwas added
  2. customthe layers were separated
  3. customthe organic layer evaporated
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-a601fd445ae04d789f75c452f7420ba9
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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