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

HRID 58636Notes

Reaction equation

HRID 58636 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-59c7c389341e4ee7bc631e5674e763b2
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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