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Sodium Carbonate → (S)-methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2'-(but-3-en-1-yl)-[1,1'-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

HRID 1400727
ノート
印刷プレビュー

反応式

HRID 1400727 の反応式
[CH2:1]([O:4][C:5]1([CH3:38])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22](Br)[CH:21]=4)[CH:19]=[C:15]3[N:14]=[C:13]([CH3:27])[C:12]=2[C@H:28]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:29]([O:31][CH3:32])=[O:30])[CH2:7][CH2:6]1)[CH:2]=[CH2:3].[CH2:39]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1B1OC(=O)CN(C)CC(=O)O1)[CH2:40][CH:41]=[CH2:42].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:4][C:5]1([CH3:38])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([C:20]4[CH:21]=[C:22]([C:44]5[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=5[CH2:39][CH2:40][CH:41]=[CH2:42])[CH:23]=[CH:24][CH:25]=4)[CH:19]=[C:15]3[N:14]=[C:13]([CH3:27])[C:12]=2[C@H:28]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:29]([O:31][CH3:32])=[O:30])[CH2:7][CH2:6]1)[CH:2]=[CH2:3]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 86710779(S)-methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetateHCID 867107802-(2-(But-3-en-1-yl)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

生成物 1

HCID 86710778(S)-methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2'-(but-3-en-1-yl)-[1,1'-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate
収率 86%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a solution of (S)-methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (250 mg, 0.427 mmol) in DMF (5 mL) was added 2-(2-(but-3-en-1-yl)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione (147 mg, 0.512 mmol), 2M sodium carbonate (0.427 mL, 0.854 mmol), and tetrakis(triphenylphosphine)palladium(0)(35 mg, 0.030 mmol). This reaction mixture was flushed with N2 and heated at 90° C. for 24 h. Upon completion of the reaction, the reaction mixture was partitioned between EtOAc and water. The organic phase was washed with water (3×), dried (MgSO4), filtered, and concentrated in vacuo to give the crude product as a brown oil. This was purified by Biotage chromatography (0-40% EtOAc/hexanes) to give 233 mg (86% yield) of (S)-methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2′-(but-3-en-1-yl)-[1,1′-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate as a colorless oil. LCMS (M+H).=637.

後処理

  1. customThis reaction mixture was flushed with N2
  2. customUpon completion of the reaction
  3. customthe reaction mixture was partitioned between EtOAc and water
  4. washThe organic phase was washed with water (3×)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the crude product as a brown oil
  9. customThis was purified by Biotage chromatography (0-40% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-9deca7ccac894aa7a02497cad34b7d28
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08906929B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート