Carbon tetrabromide → 3-(2-bromoethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile

HRID 1918625Notes

Reaction equation

HRID 1918625 reaction equation
O[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]#[N:14])[CH:11]=2)[NH:6][C:5]=1[Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:41]C(Br)(Br)Br>C1COCC1>[Br:41][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]#[N:14])[CH:11]=2)[NH:6][C:5]=1[Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 668321333-(2-hydroxyethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile

Product 1

HCID 668319283-(2-bromoethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrileYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution 3-(2-hydroxyethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile (0.873 g; 2.91 mmol) in THF (6 mL) was added to a solution of triphenylphosphine (1.52 g; 5.81 mmol) and perbromomethane (1.93 g; 5.81 mmol) in THF (30 mL) pre-stirred for 30 minutes. The resulting mixture was stirred at room temperature overnight, filtered and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 2 to 40% ethyl acetate in heptane) to yield 0.906 g (86%) of the title compound as a white solid.

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe crude mixture was purified by flash chromatography on silica (eluent 2 to 40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-4a004be41fea4e2291927934bc72f431
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

Loading…