Carbon tetrabromide → N-[4-(bromomethyl)-6-chloropyridin-2-yl]-N-propylmethanesulfonamide

HRID 552890Notes

Reaction equation

HRID 552890 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH2:13][CH2:14][CH3:15])[S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[C:4]([CH2:16]O)[CH:3]=1.C(Br)(Br)(Br)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:19][CH2:16][C:4]1[CH:3]=[C:2]([Cl:1])[N:7]=[C:6]([N:8]([CH2:13][CH2:14][CH3:15])[S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57775667N-[6-chloro-4-(hydroxymethyl)pyridin-2-yl]-N-propylmethanesulfonamide

Product 1

HCID 59650918N-[4-(bromomethyl)-6-chloropyridin-2-yl]-N-propylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[6-chloro-4-(hydroxymethyl)pyridin-2-yl]-N-propylmethanesulfonamide (740 mg, 2.65 mmol) in dichloromethane (20 mL) cooled to 0° C. was added carbon tetrabromide (967 mg, 2.92 mmol) and triphenylphosphine (765 mg, 2.92 mmol). After 10 min, the reaction mixture was allowed to warm to rt and stirred for 0.5 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography (silica, 0-25% EtOAc/hexanes) to provide N-[4-(bromomethyl)-6-chloropyridin-2-yl]-N-propylmethanesulfonamide as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.34 (s, 1H), 7.22 (s, 1H), 4.35 (s, 2H), 3.85 (t, J=7.6 Hz, 2H), 3.04 (s, 3H), 1.64-1.50 (m, 2H), 0.93 (t, J=7.2 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by flash chromatography (silica, 0-25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2e8a0f4a0a3c4e919670f920ca86f001
Source dataset
uspto-grants-2011_05
Patent number
US07951949B2

Reaction notes

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