Acetic Acid → HCID 66907651, compound

HRID 1691827Notes

Reaction equation

HRID 1691827 reaction equation
C(O)(=O)C.C1COCC1.[Br:10][C:11]1[CH:16]=[C:15]([Cl:17])[C:14]([CH:18]([O:20][Si](C(C)(C)C)(C)C)[CH3:19])=[CH:13][C:12]=1[NH:28][C:29]([N:31]1[CH:36]=[CH:35][C:34](=[O:37])[CH2:33][CH:32]1[C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=1)=[O:30]>O>[Br:10][C:11]1[CH:16]=[C:15]([Cl:17])[C:14]([CH:18]([OH:20])[CH3:19])=[CH:13][C:12]=1[NH:28][C:29]([N:31]1[CH:36]=[CH:35][C:34](=[O:37])[CH2:33][CH:32]1[C:38]1[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=1)=[O:30]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 66907580HCID 66907580, compound

Product 1

HCID 66907651HCID 66907651, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of acetic acid (4.5 ml), water (1.5 ml) and THF (1.5 ml) was added to a flask containing 2-(4-fluoro-phenyl)-4-oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid {2-bromo-5-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-chloro-phenyl}-amide (0.144 g, 0.247 mmol). The mixture was stirred at room temperature for 16 hours. Water was added and the mixture was extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification by flash chromatography (EtOAc) gave 2-(4-fluoro-phenyl)-4-oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid [2-bromo-4-chloro-5-(1-hydroxy-ethyl)-phenyl]-amide (0.082 g, 71%) as a white foam. MS (M+H) 468.

Workup

  1. additionwas added to a flask
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-f7dc8e48f4e7438facdbf10e61d9f149
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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