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

HRID 859153

反応式

HRID 859153 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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)−.

後処理

  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

出典と根拠

ORDレコード
ord-ef20ac88098c4840874085078ec9fcd5
出典データセット
uspto-grants-2006_12
特許番号
US07151112B1

関連ノート

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