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

HRID 563402노트

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HRID 563402 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
85 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7239e854cb5047679ec6649465c94480
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067447B2

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