Sodium Bicarbonate → 2,6-Difluoro-N-(1-{[2-methyl-6-(methyloxy)phenyl]methyl}-1H-pyrazol-3-yl)benzamide

HRID 1946429노트

반응식

HRID 1946429 반응식
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][NH:9][N:8]=1)=[O:5].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:28][C:29]1[C:34]([O:35][CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=1[CH3:37].C(=O)(O)[O-].[Na+]>C1COCC1>[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:28][C:29]2[C:34]([O:35][CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:37])[N:8]=1)=[O:5]

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 2733832Lithium HexamethyldisilazideHCID 103532222-(Bromomethyl)-1-methoxy-3-methylbenzeneHCID 178522346HCID 178522346, 화합물2회

생성물 1

HCID 595478822,6-Difluoro-N-(1-{[2-methyl-6-(methyloxy)phenyl]methyl}-1H-pyrazol-3-yl)benzamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a stirred solution of 2,6-difluoro-N-1H-pyrazol-3-ylbenzamide (for a preparation see Intermediate 9)(50 mg, 0.224 mmol) in dry THF (1.75 ml) under nitrogen was added 1.0 lithium bis(trimethylsilyl)amide in THF (0.2 ml, 0.2 mmol) dropwise and the solution stirred for 30 min. To the solution was added a solution of 2-(bromomethyl)-1-methyl-3-(methyloxy)benzene (for a preparation see intermediate 57)(48 mg, 0.224 mmol) in THF (1.75 ml). The solution was stirred for 1.5 h and then allowed to stand overnight. The solvent was blown down using a stream of nitrogen and aqueous sodium bicarbonate added to the residue. The aqueous phase was then extracted with chloroform. The organic extract was removed in vacuo to give a gum (84 mg). The residue was purified on MDAP (Method B). The solvent was removed and the residue dried at −45° C. under high vacuum to give the title compound as a white solid; LCMS (System 4) MH+=358, tRET=2.77 min.

후처리

  1. stirringThe solution was stirred for 1.5 h
  2. waitto stand overnight
  3. additionadded to the residue
  4. extractionThe aqueous phase was then extracted with chloroform
  5. extractionThe organic extract
  6. customwas removed in vacuo

출처 및 근거

ORD 기록
ord-efa263d39ff6450c8b722cf66a86b939
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399436B2

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