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

HRID 925311Notes

Reaction equation

HRID 925311 reaction equation
[CH2:1]([Si:3]([CH2:22][CH3:23])([CH2:20][CH3:21])[C:4]1[NH:5][C:6]2[C:11]([C:12]=1[CH2:13][CH2:14]O)=[CH:10][C:9]([C:16]([F:19])([F:18])[F:17])=[CH:8][CH:7]=2)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:43]C(Br)(Br)Br>C1COCC1>[Br:43][CH2:14][CH2:13][C:12]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:16]([F:19])([F:18])[F:17])[CH:10]=2)[NH:5][C:4]=1[Si:3]([CH2:22][CH3:23])([CH2:20][CH3:21])[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 668320092-(2-(triethylsilyl)-5-(trifluoromethyl)-1H-indol-3-yl)ethanol

Product 1

HCID 668317303-(2-bromoethyl)-2-(triethylsilyl)-5-(trifluoromethyl)-1H-indoleYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(2-bromoethyl)-2-(triethylsilyl)-5-(trifluoromethyl)-1H-indole was prepared according to method D Step III with 2-(2-(triethylsilyl)-5-(trifluoromethyl)-1H-indol-3-yl)ethanol (0.730 g; 2.13 mmol) in THF (6 mL); triphenyl phosphine (0.836 g; 3.19 mmol) and perbromomethane (1.06 g; 3.19 mmol) in THF (12 mL) pre-stirred for 1 hour. The crude residue was purified by flash chromatography on silica gel (eluent 5 to 40% ethyl acetate in heptane) to afford 0.449 g (52%) of 3-(2-bromoethyl)-2-(triethylsilyl)-5-(trifluoromethyl)-1H-indole as a yellow oil.

Workup

  1. custom3-(2-bromoethyl)-2-(triethylsilyl)-5-(trifluoromethyl)-1H-indole was prepared
  2. customThe crude residue was purified by flash chromatography on silica gel (eluent 5 to 40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-6edfe16c60db4145b4e51b04e2b106a1
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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