HCID 58138925, compound → HCID 58138929, compound

HRID 73227Notes

Reaction equation

HRID 73227 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]#[N:13])=[CH:7][C:6]=2[Br:14]>C1COCC1>[F:16][C:2]([F:1])([F:15])[C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][NH2:13])=[CH:7][C:6]=2[Br:14]

Participants

3

Reactant 1

HCID 58138925HCID 58138925, compound2×

Product 1

HCID 58138929HCID 58138929, compoundYield 113.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(trifluoromethyl)-5-cyano-7-bromo-1H-indole (Intermediate 4, 200 mg) in THF (10 mL) cooled in an ice-water bath was treated with borane tetrahydrofuran complex (1.52 mL) dropwise via a syringe and stirred under argon for 18 hrs while allowing to warm to room temp. The reaction mixture was then quenched with methanol (5 mL) and stirred at room temperature for 10 min. The reaction mixture was then evaporated to dryness to give the title compound as a white foam (230 mg), which was used in the next step without further purification;

Workup

  1. additionwas treated with borane tetrahydrofuran complex (1.52 mL) dropwise via a syringe
  2. customThe reaction mixture was then quenched with methanol (5 mL)
  3. stirringstirred at room temperature for 10 min
  4. customThe reaction mixture was then evaporated to dryness

Sources & evidence

ORD record
ord-01cd1980e8b54705a7a31db1c379ac08
Source dataset
uspto-grants-2014_09
Patent number
US08829031B2

Reaction notes

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