Cesium carbonate → HCID 57831043、化合物

HRID 600394ノート

反応式

HRID 600394 の反応式
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2=[N:6][CH:7]=1.[C:25](=[NH:38])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:25](=[N:38][C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2=[N:6][CH:7]=1)([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 578292211-(2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-yl)-2,2-dimethylpropane-1-one

生成物 1

HCID 57831043HCID 57831043、化合物収率 93.3%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
90 °C

実験手順

A mixture of 1-[2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.576 g, 1.40 mmol), benzophenone imine (0.26 mL, 1.54 mmol), cesium carbonate (0.912 g, 2.80 mmol), palladium acetate (0.031 g, 0.14 mmol) and BINAP (0.087 g, 0.14 mmol) in 14 mL of tetrahydrofuran was stirred at 90° C. in a sealed tube for 64 h then concentrated. The resulting residue was taken up in 30 mL of ethyl acetate and sequentially washed with 30 mL of water and 30 mL of a sat. aq. NaCl solution, dried over MgSO4, filtered and concentrated to a residue. Column chromatography (10→25% EtOAc/hexanes) afforded 0.670 g (93%) of 1-[2-(benzhydrylidene-amino)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow oil.

後処理

  1. concentrationthen concentrated
  2. washsequentially washed with 30 mL of water and 30 mL of a sat. aq. NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a residue

出典と根拠

ORDレコード
ord-2f4f7688aacc424994bf6c96cc3b9cf4
出典データセット
uspto-grants-2011_03
特許番号
US07902197B2

反応ノート

読み込み中…