Sodium Bicarbonate → 6-(2-benzyloxy-6-chloro-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

HRID 469319Notes

Reaction equation

HRID 469319 reaction equation
[Na].Cl[C:3]1[CH:8]=[C:7]([C:9]([C:11]2[CH:20]=[C:19]([CH3:21])[C:14]3[NH:15][C:16](=[O:18])[O:17][C:13]=3[CH:12]=2)=[O:10])[CH:6]=[C:5]([Cl:22])[N:4]=1.[C:23](=[O:26])([O-])O.[Na+]>C1COCC1>[CH2:23]([O:26][C:3]1[CH:8]=[C:7]([C:9]([C:11]2[CH:20]=[C:19]([CH3:21])[C:14]3[NH:15][C:16](=[O:18])[O:17][C:13]=3[CH:12]=2)=[O:10])[CH:6]=[C:5]([Cl:22])[N:4]=1)[C:11]1[CH:20]=[CH:19][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 581812126-(2,6-dichloro-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 581811156-(2-benzyloxy-6-chloro-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.85 mL (3.85 mmol) sodium benzylate solution (1M in benzylalcohol) were added to 1.24 g (3.85 mmol) 6-(2,6-dichloro-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one in 50 mL THF and stirred overnight at RT. The reaction mixture was combined with saturated sodium hydrogen carbonate solution and extracted with EtOAc. The combined organic phases were dried and evaporated down i. vac.

Workup

  1. extractionextracted with EtOAc
  2. customThe combined organic phases were dried
  3. customevaporated down i

Sources & evidence

ORD record
ord-ccebd0ecd7dd43619df8b69ad3d07c11
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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