Carbon tetrabromide → 6-Bromomethyl-5-cyclopropyl-pyridine-2-carbonitrile

HRID 624850Notes

Reaction equation

HRID 624850 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:12]#[N:13])=[N:8][C:9]=2[CH2:10]O)[CH2:3][CH2:2]1.C(Br)(Br)(Br)[Br:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[Br:15][CH2:10][C:9]1[N:8]=[C:7]([C:12]#[N:13])[CH:6]=[CH:5][C:4]=1[CH:1]1[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 866747715-Cyclopropyl-6-hydroxymethyl-pyridine-2-carbonitrile

Product 1

HCID 866747706-Bromomethyl-5-cyclopropyl-pyridine-2-carbonitrileYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-cyclopropyl-6-hydroxymethyl-pyridine-2-carbonitrile (0.1 g, 0.6 mmol), CBr4 (0.8 g, 1.2 mmol), PPh3 (0.3 g, 1.2 mmol) in THF (10 mL) was stirred for 12 h at 40° C. The solvent was removed under reduced pressure and the crude product purified by flash column chromatography (silica gel, 3 g, eluting with 25% ethyl acetate in petroleum ether) to give the title compound (0.1 g, 74%) as yellow solid; MS (EI): m/e=236.9 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product purified by flash column chromatography (silica gel, 3 g, eluting with 25% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-43a57f817ee7458b911e00a17e6817c0
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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