Methanesulfonyl chloride → HCID 68511606, compound

HRID 1716295Notes

Reaction equation

HRID 1716295 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl.N1C=CC=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][N:11]([C:12]2[CH:13]=[CH:14][C:15]([O:18][C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[CH:16][CH:17]=2)[S:27]([CH3:26])(=[O:29])=[O:28])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68512931HCID 68512931, compound

Product 1

HCID 68511606HCID 68511606, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21875418Pyridine methylene chlorideSolvent

Procedure

To a solution of (5-bromo-2-methoxy-pyridin-3-ylmethyl)-(4-p-tolyloxy-phenyl)-amine (0.73 g, 1.82 mmol) from Step A in CH2Cl2/pyridine (6 mL/3 mL) was dropwise added methylsulfonyl chloride (0.17 mL, 2.2 mmol) at 0° C. The resulting mixture was warmed to room temperature and stirred overnight. The reaction was then diluted with CH2Cl2 and washed with aqueous HCl (3N) to remove pyridine. The organic layer was then brought to the usual work-up. The crude product was purified by chromatography (silica gel, 30% EtOAc/hexanes). MS (EI) 477, 479 (M+H)+.

Workup

  1. customat 0° C
  2. washwashed with aqueous HCl (3N)
  3. customto remove pyridine
  4. customThe crude product was purified by chromatography (silica gel, 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6622d5547d9c4579bbe6e7789cc39e28
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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