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Sodium hydride → 1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-3-tetrahydropyran-4-yl-propan-1-one

HRID 710666
ノート
印刷プレビュー

反応式

HRID 710666 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:17](=[O:29])[CH2:18][N:19]4[C:23]([CH3:24])=[CH:22][C:21]([C:25]([F:28])([F:27])[F:26])=[N:20]4)[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.I[CH2:31][CH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.[H-].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:17](=[O:29])[CH:18]([N:19]4[C:23]([CH3:24])=[CH:22][C:21]([C:25]([F:27])([F:26])[F:28])=[N:20]4)[CH2:31][CH:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)[C:11]=3[CH:10]=[N:9]2)=[CH:6][CH:7]=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 24758Sodium hydrideHCID 27955074-(Iodomethyl)oxaneHCID 733351261-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone

生成物 1

HCID 730569281-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-3-tetrahydropyran-4-yl-propan-1-one収率 6%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

A mixture of 1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone (0.100 g, 0.25 mmol), 4-(iodomethyl)tetrahydro-2H-pyran (0.165 g, 0.75 mmol) and NaH (0.030 g, 0.75 mmol, 60% in mineral oil) in DMF (0.8 mL) was stirred at rt for 1.5 hrs. It was then quenched with sat. NH4Cl. The mixture was partitioned between EtOAc (50 mL) and brine (30 mL). The organic layer was separated, dried over Na2SO4, concentrated in vacuo, and purified by reverse phase HPLC to afford the desired product (0.007 g, 6%). 1H NMR (400 MHz, CDCl3) δ 8.44 (s, 1H), 7.43 (dd, J=8.8, 4.8 Hz, 2H), 7.16 (dd, J=8.8, 8.4 Hz, 2H), 6.31 (s, 1H), 5.54 (m, 1H), 3.95 (m, 2H), 3.78 (m, 1H), 3.47 (m, 1H), 3.34 (m, 2H), 2.75 (m, 2H), 2.30 (s, 3H), 2.20 (m, 3H), 1.88 (m, 3H), 1.40 (m, 3H); MS: (ES) m/z calculated for C25H27F4N5O2 [M+H]+ 506.2, found 506.2.

後処理

  1. customIt was then quenched with sat. NH4Cl
  2. customThe mixture was partitioned between EtOAc (50 mL) and brine (30 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by reverse phase HPLC

出典と根拠

ORDレコード
ord-eaeeb72529b4406da9a0a64f1800bd22
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181241B2

反応ノート

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