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

HRID 859153

반응식

HRID 859153 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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)−.

후처리

  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

출처 및 근거

ORD 기록
ord-ef20ac88098c4840874085078ec9fcd5
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07151112B1

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