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

HRID 1777543Notes

Reaction equation

HRID 1777543 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

A solution 2-(2-(triethylsilyl)-5-(trifluoromethyl)-1H-indol-3-yl)ethanol (0.730 g; 2.13 mmol) in THF (6 mL) was added to a solution of triphenylphosphine (0.836 g; 3.19 mmol) and perbromomethane (1.06 g; 3.19 mmol) in THF (12 mL) pre-stirred for 1 hour. The resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was then filtered and concentrated under reduced pressure. 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 the title compound as a yellow oil.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 18 hours
  2. filtrationThe reaction mixture was then filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was purified by flash chromatography on silica gel (eluent 5 to 40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-22cc35ba349b47b69321ea2f64dcc0ac
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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