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Potassium Carbonate → N-[1-({4-Chloro-2-[(phenylmethyl)oxy]phenyl]methyl)-1H-pyrazol-3-yl}-2,6-difluorobenzamide

HRID 1946362
ノート
印刷プレビュー

反応式

HRID 1946362 の反応式
[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(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=1[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C=O)C>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:9]2[CH:10]=[CH:11][C:7]([NH:6][C:4](=[O:5])[C:3]3[C:12]([F:16])=[CH:13][CH:14]=[CH:15][C:2]=3[F:1])=[N:8]2)=[C:26]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:27]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 667254251-(Bromomethyl)-4-chloro-2-[(phenylmethyl)oxy]benzeneHCID 178522346HCID 178522346、化合物2 回

生成物 1

HCID 59547907N-[1-({4-Chloro-2-[(phenylmethyl)oxy]phenyl]methyl)-1H-pyrazol-3-yl}-2,6-difluorobenzamide収率 17.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 2,6-difluoro-N-1H-pyrazol-3-ylbenzamide (for as preparation see Intermediate 9) (76 mg, 0.340 mmol) and potassium carbonate (96 mg, 0.692 mmol) was added a solution of 1-(bromomethyl)-4-chloro-2-[(phenylmethyl)oxy]benzene (0.106 g, 0.340 mmol) in DMF (1 ml). The reaction was stirred overnight, at ambient temperature and under nitrogen. The suspension was filtered using a hydrophobic frit and the residue washed with methanol (1 ml). The filtrate was purified by MDAP (supelcosil ABZ+Plus column) eluting with solvents A/B (A: Water+0.1% Formic acid, B: MeCN:Water 95:5+0.05% Formic acid) (Method A). The solvent was evaporated in vacuo to give the title compound as a white solid (27 mg); LCMS: (System 1) MH+=454, tRET=3.68 min.

後処理

  1. filtrationThe suspension was filtered
  2. washthe residue washed with methanol (1 ml)
  3. customThe filtrate was purified by MDAP (supelcosil ABZ+Plus column)
  4. washeluting with solvents A/B (A: Water+0.1% Formic acid, B
  5. customThe solvent was evaporated in vacuo

出典と根拠

ORDレコード
ord-354a4c80a678449992d4bf4bcda519d1
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08399436B2

反応ノート

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