Methyl iodide → 6-(5-bromo-pyridin-3-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

HRID 469327Notes

Reaction equation

HRID 469327 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([C:10]([C:12]2[CH:21]=[C:20]([CH3:22])[C:15]3[NH:16][C:17](=[O:19])[O:18][C:14]=3[CH:13]=2)=[O:11])[CH:7]=[N:8][CH:9]=1.I[CH3:24]>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]([C:10]([C:12]2[CH:21]=[C:20]([CH3:22])[C:15]3[N:16]([CH3:24])[C:17](=[O:19])[O:18][C:14]=3[CH:13]=2)=[O:11])[CH:7]=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 581811166-(5-bromo-pyridin-3-carbonyl)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 581811706-(5-bromo-pyridin-3-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.18 g (4.00 mmol) sodium hydride (55%, suspension in mineral oil) were added at RT to 1.27 g (3.80 mmol) 6-(5-bromo-pyridin-3-carbonyl)-4-methyl-3H-benzoxazol-2-one in 5 mL DMF. The reaction mixture was stirred for 30 min at RT. Then 0.32 mL (5.00 mmol) iodomethane were added and the mixture was stirred overnight at RT. The reaction mixture was poured onto ice water and the precipitate formed was suction filtered, washed with water and dried i. vac.

Workup

  1. stirringthe mixture was stirred overnight at RT
  2. additionThe reaction mixture was poured onto ice water
  3. customthe precipitate formed
  4. filtrationfiltered
  5. washwashed with water
  6. customdried i

Sources & evidence

ORD record
ord-9ec82906a2194e2cb50588c360675d1d
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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