Carbon tetrabromide → 3-(2-bromoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine

HRID 925324

Reaction equation

HRID 925324 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][CH2:12]O)=[C:9]([Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16])[NH:8][C:5]2=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:40]C(Br)(Br)Br>C1COCC1>[Br:40][CH2:12][CH2:11][C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[NH:8][C:9]=1[Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 110560231H-Pyrrolo[2,3-B]pyridine-3-ethanol, 5-chloro-2-(triethylsilyl)-

Product 1

HCID 668319713-(2-bromoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridineYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(2-bromoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine was prepared according to method D Step III with 2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol (2.0 g; 6.43 mmol) in THF (30 mL) and triphenyl phosphine (2.56 g; 9.65 mmol) and perbromomethane (3.27 g, 9.65 mmol) in THF (40 mL) pre-stirred for 30 minutes. The crude mixture was purified by flash chromatography on silica gel (eluent 5 to 40% of ethyl acetate in heptanes) to yield 1.08 g (45%) of 3-(2-bromoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine as a white solid.

Workup

  1. custom3-(2-bromoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine was prepared
  2. customThe crude mixture was purified by flash chromatography on silica gel (eluent 5 to 40% of ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-e4e293e557a54432b8d84b3b6b57f311
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Linked notes

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