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

HRID 925315Notes

Reaction equation

HRID 925315 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

3-(2-bromoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indole was prepared according to method D Step III with 2-(6-chloro-5-methyl-2-(triethylsilyl)-1H-indol-3-yl)ethanol (1.44 g; 4.45 mmol) in THF (6 mL) and triphenyl phosphine (1.75 g; 6.67 mmol) and perbromomethane (2.21 g; 6.67 mmol) in THF (40 mL) pre-stirred for 30 minutes. The crude mixture was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford 0.725 g (42%) of 3-(2-bromoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indole as a brown oil.

Workup

  1. custom3-(2-bromoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indole was prepared
  2. customThe crude mixture was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-a1bc07ea1c9d4b6cab9b4c59c5027471
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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