2-Amino-6-bromopyridine → HCID 58988141, compound

HRID 2234974Notes

Reaction equation

HRID 2234974 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:12].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[N:15]=1>ClCCl.N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[N:15]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:12]

Participants

5

Reactant 2

HCID 3008092-Amino-6-bromopyridineHCID 27782184-Bromo-3-fluorobenzenesulfonyl chloride

Product 1

HCID 58988141HCID 58988141, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromo-3-fluorobenzenesulfonyl chloride (684 mg, 370 μl, 2.5 mmol) in dichloromethane (2 ml) was added slowly at room temperature to a solution of 2-amino-6-bromopyridine (346 mg, 2.0 mmol) in pyridine (2 ml). The reaction mixture was stirred at room temperature for 1 h. The solvent was evaporated and the residue partitioned between ethyl acetate (50 ml) and water (50 ml). The organic phase washed with water (×2), separated, dried and evaporated. Purification by column chromatography eluting with 20-60% ethyl acetate in hexanes afforded the title compound (D1), MS (ES+) m/e 409, 411, 413 [M+H]+.

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate (50 ml) and water (50 ml)
  3. washThe organic phase washed with water (×2)
  4. customseparated
  5. customdried
  6. customevaporated
  7. customPurification by column chromatography
  8. washeluting with 20-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8d95c41c92fd4af3b52bae017150d4c3
Source dataset
uspto-grants-2010_05
Patent number
US07713978B2

Reaction notes

Loading…