Carbon tetrabromide → 3-(2-bromoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indole

HRID 1777548Notes

Reaction equation

HRID 1777548 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:18][CH2:19]O)=[C:7]([Si:11]([CH2:16][CH3:17])([CH2:14][CH3:15])[CH2:12][CH3:13])[NH:8]2)=[CH:4][C:3]=1[CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:41]C(Br)(Br)Br>C1COCC1>[Br:41][CH2:19][CH2:18][C:6]1[C:5]2[C:9](=[CH:10][C:2]([Cl:1])=[C:3]([CH3:21])[CH:4]=2)[NH:8][C:7]=1[Si:11]([CH2:16][CH3:17])([CH2:14][CH3:15])[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 668320342-(6-chloro-5-methyl-2-(triethylsilyl)-1H-indol-3-yl)ethanol

Product 1

HCID 668318963-(2-bromoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indoleYield 42.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(6-chloro-5-methyl-2-(triethylsilyl)-1H-indol-3-yl)ethanol (1.44 g; 4.45 mmol) in THF (6 mL) was added to a solution of triphenylphosphine (1.75 g; 6.67 mmol) and perbromomethane (2.21 g; 6.67 mmol) in THF (40 mL) pre-stirred for 30 minutes. 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 2 to 20% ethyl acetate in heptane) to afford 0.725 g (42%) of the title compound as a brown 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 2 to 20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-bd4d2e95b66043fc96794454dab1a0ec
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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