Carbon tetrabromide → Tert-butyl 3-(bromomethyl)-4-fluoropyridin-2-ylcarbamate

HRID 920126

Reaction equation

HRID 920126 reaction equation
[C:1]([Br:5])(Br)(Br)Br.[F:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]=1CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:5][CH2:1][C:8]1[C:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[N:10][CH:11]=[CH:12][C:7]=1[F:6]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 89656375[2-(Boc-amino)-4-fluoropyridin-3-yl]methanol

Product 1

HCID 89656446Tert-butyl 3-(bromomethyl)-4-fluoropyridin-2-ylcarbamateYield 52.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

CBr4 (531 mg, 1.6 mmol) was added to a solution of the product of Step B (242 mg, 1 mmol) in THF (3 mL). Then a solution of triphenylphosphine in THF (1 mL) was added dropwise and the mixture was stirred at room temperature for 3 hours. The mixture was loaded onto a silica gel column. Elution with (EtOAc:PE=1:3) to afford the title compound (160 mg, 52%) as a white solid. 1H-NMR (400 MHz, CDCl3) δ 8.38-8.35 (m, 1H), 7.09 (s, 1H), 6.90-6.86 (m, 1H), 4.61 (s, 2H), 1.54 (s, 9H) ppm MS: M/e 305 (M+1)+.

Workup

  1. washElution with (EtOAc:PE=1:3)

Sources & evidence

ORD record
ord-b5a4c0e78aa4463aab5af3e5f0017092
Source dataset
uspto-grants-2016_03
Patent number
US09273046B2

Linked notes

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