Dimethylformamide → (E)-methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylacrylate

HRID 563402ノート

反応式

HRID 563402 の反応式
C[C:2](P(OC)(O)=O)([C:4]([O-:6])=[O:5])C.[Na].[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:28]3[C:23](=[CH:24][C:25]([C:29]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=O)=[CH:26][CH:27]=3)[CH:22]=[N:21]2)=[CH:16][CH:15]=1.[CH3:37]N(C=O)C>C1COCC1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:28]3[C:23](=[CH:24][C:25](/[C:29](/[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:2]/[C:4]([O:6][CH3:37])=[O:5])=[CH:26][CH:27]=3)[CH:22]=[N:21]2)=[CH:16][CH:15]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 5360545SodiumHCID 53413272TrimethylphosphonoacetateHCID 67005723(1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanone

生成物 1

HCID 59252822(E)-methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylacrylate収率 91%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
85 °C

実験手順

Trimethylphosphonoacetate (2.4 g, 13.4 mmol) was dissolved in 15 mL anhydrous DMF and treated with sodium hexadimethylsilazane (13.4 mmol, 1 M in THF). (1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanone (1.63 g, 5.16 mmol) was added and the reaction was heated to 85° C. for 16 hours. The following day, the cooled reaction was extracted from brine using ether×3 and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel using 25% EtOAc in hexanes to give 1.74 g (91%) of (E)-methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-phenylacrylate as a clear oil. MS found: (M+H)+=373.

後処理

  1. customThe following day, the cooled reaction
  2. extractionwas extracted from brine
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel using 25% EtOAc in hexanes

出典と根拠

ORDレコード
ord-7239e854cb5047679ec6649465c94480
出典データセット
uspto-grants-2011_11
特許番号
US08067447B2

反応ノート

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