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Water → 2-(6-(1-benzyl-1H-pyrazol-4-yl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)-6,6-dimethyl-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one

HRID 885960
ノート
印刷プレビュー

反応式

HRID 885960 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([C:11]3[S:12][C:13]4[CH2:14]C(C)(C)N[C:17](=O)[C:18]=4[N:19]=3)[C:6]=2[CH:23]=1.[CH2:24]([N:31]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[N:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+].[OH2:51]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.CCOC(C)=O>[CH2:24]([N:31]1[CH:35]=[C:34]([C:2]2[CH:3]=[CH:4][C:5]3[O:10][CH2:9][CH2:8][N:7]([C:11]4[S:12][C:13]5[C:14](=[O:51])[NH:7][C:6]([CH3:23])([CH3:5])[CH2:17][C:18]=5[N:19]=4)[C:6]=3[CH:23]=2)[CH:33]=[N:32]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27347711-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 685972362-(6-Bromo-2,3-dihydrobenzo[1,4]oxazin-4-yl)-6,6-dimethyl-6,7-dihydro-[1,3]thiazolo[5,4-d]pyridin-4(5h)-one

生成物 1

HCID 445807222-(6-(1-benzyl-1H-pyrazol-4-yl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)-6,6-dimethyl-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one
収率 68%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A stirred solution of Example 39 (0.051 g, 0.129 mmol), 1-benzyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.049 g, 0.173 mmol), K2CO3 (0.054 g, 0.388 mmol), tetra-n-butylammonium bromide (0.124 g, 0.385 mmol), tetrakis-(triphenylphosphine)palladium(0) (0.010 g, 0.009 mmol) and H2O (0.5 mL) in THF (1 mL) was heated to 125° C. under microwave irradiation for 1 h. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic fractions were dried (MgSO4), filtered and concentrated in vacuo. The crude material was triturated with Et2O to give the title compound (0.041 g, 68%) as a beige solid. δH (CDCl3) 8.03 (1H, d, J 1.9 Hz), 7.78 (1H, s), 7.60 (1H, s), 7.40-7.25 (5H, m), 7.18 (1H, dd, J 8.5 and J 2.1 Hz), 6.96 (1H, d, J 8.3 Hz), 5.37 (2H, s), 5.26 (1H, br. s), 4.38-4.32 (2H, m), 4.22-4.16 (2H, m), 2.89 (2H, s), 1.42 (6H, s). LCMS (ES+) 472.0 (M+H)+, RT 3.53 minutes (Method 1).

後処理

  1. washwashed with water and brine
  2. dry with materialThe organic fractions were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was triturated with Et2O

出典と根拠

ORDレコード
ord-08c3178ca4bb4603b45f155768738a38
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08242116B2

反応ノート

読み込み中…

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