Ethyl Acetate → [5-(4-Fluorophenylcarbamoyl)Pyridin-2-Ylsulfanyl]Acetic Acid Propyl Ester

HRID 859153

Reaction equation

HRID 859153 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13]([SH:16])=[N:12][CH:11]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:25][C:26]([O:28][CH2:29][CH2:30][CH3:31])=[O:27].C(OCC)(=O)C>CN(C=O)C.O>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][S:16][C:13]1[CH:14]=[CH:15][C:10]([C:9](=[O:17])[NH:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:11][N:12]=1)[CH2:30][CH3:31]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 141981Acetic acid, bromo-, propyl esterHCID 178522139HCID 178522139, compound

Product 1

HCID 12146502[5-(4-Fluorophenylcarbamoyl)Pyridin-2-Ylsulfanyl]Acetic Acid Propyl EsterYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of of N-(4-fluorophenyl)-6-mercaptonicotinamide (0.024 g, 0.097 mmol, see Example 1) in 2 mL of DMF was added cesium carbonate (0.094 g, 0.29 mmol) and propyl bromoacetate (0.025 μL). The mixture was stirred for 30 minutes and poured into ethyl acetate and water. The organic layer was removed, dried over sodium sulfate, filtered, and the solvents removed in vacuo. Purification by trituration using ethyl acetate/hexanes gave 34 mg (76%) of the titled product as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 10.36 (s 1H), 8.88 (m, 1H), 8.12 (m, 1H), 7.73 (m, 2H), 7.49 (m, 1H), 7.18 (m, 2H), 4.09 (s, 2H), 4.02 (m, 2H), 1.54 (m, 2H), 0.82 (m, 3H); MS (EI) m/z 347.06 (M−H)−.

Workup

  1. customThe organic layer was removed
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvents removed in vacuo
  5. customPurification by trituration

Sources & evidence

ORD record
ord-ef20ac88098c4840874085078ec9fcd5
Source dataset
uspto-grants-2006_12
Patent number
US07151112B1

Linked notes

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