2-Amino-5-bromopyridine → HCID 86662066, compound

HRID 1907339Notes

Reaction equation

HRID 1907339 reaction equation
[C:1]1([CH3:14])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O:12][NH2:13])(=[O:11])=[O:10].[Br:15][C:16]1[CH:17]=[CH:18][C:19]([NH2:22])=[N:20][CH:21]=1>ClCCl>[CH3:8][C:3]1[CH:4]=[C:5]([CH3:7])[CH:6]=[C:1]([CH3:14])[C:2]=1[S:9]([O-:12])(=[O:11])=[O:10].[NH2:13][N+:20]1[CH:21]=[C:16]([Br:15])[CH:17]=[CH:18][C:19]=1[NH2:22]

Participants

4

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 86662066HCID 86662066, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

O-(Mesitylsulfonyl)hydroxylamine (3.84 g) dissolved in dichloromethane (150 mL) was added over a period of 1 h to a stirred solution of 5-bromo-pyridin-2-ylamine (3.00 g) in dichloromethane (100 mL) chilled in an ice bath. The cooling bath was removed and the mixture was stirred at room temperature for 15 min. The precipitate was separated by filtration, washed with dichloromethane, and dried to give the title compound as a colorless solid. Yield: 5.04 g (75% of theory); Mass spectrum (ESI+): m/z=188/200 (Br) [M1+H]+; Mass spectrum (ESI): m/z=199 [M2−H]−.

Workup

  1. temperaturechilled in an ice bath
  2. customThe cooling bath was removed
  3. customThe precipitate was separated by filtration
  4. washwashed with dichloromethane
  5. customdried

Sources & evidence

ORD record
ord-6e25ff3792f746aa81e5cd2527cc45c4
Source dataset
uspto-grants-2013_12
Patent number
US08598163B2

Reaction notes

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