Borane;tetrahydrofuran → HCID 58138929, compound

HRID 2061566Notes

Reaction equation

HRID 2061566 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].O1CCCC1.B>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

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 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 8; 200 mg, 0.692 mmol) in THF (10 mL) cooled in an ice-water bath was treated with borane tetrahydrofuran complex (1M in THF, 1.522 mL, 1.522 mmol) 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. customThe reaction mixture was then quenched with methanol (5 mL)
  2. stirringstirred at room temperature for 10 min
  3. customThe reaction mixture was then evaporated to dryness

Sources & evidence

ORD record
ord-72fa84c93b0e4efd81edddfde4ab4e85
Source dataset
uspto-grants-2012_10
Patent number
US08283365B2

Reaction notes

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