Trimethyl phosphite → 3-(Isoquinolin-4-yl)acrylic Acid t-Butyl Ester

HRID 220264

反応式

HRID 220264 の反応式
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.[C:12]([O:16][C:17](=[O:20])[CH:18]=[CH2:19])([CH3:15])([CH3:14])[CH3:13].CCN(C(C)C)C(C)C.P(OC)(OC)OC>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:12]([O:16][C:17](=[O:20])[CH:18]=[CH:19][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1)([CH3:15])([CH3:14])[CH3:13]

参加物

7

反応物 4

HCID 8472Trimethyl phosphiteHCID 15458tert-Butyl acrylateHCID 737434-BromoisoquinolineHCID 81531Diisopropylethylamine

生成物 1

HCID 684144603-(Isoquinolin-4-yl)acrylic Acid t-Butyl Ester

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

To a mixture of 3 g of 4-bromoisoquinoline, 6.2 mL of acrylic acid tert.-butyl ester and 2.66 mL of DIPEA in 30 mL of DMF under argon was added 0.169 mL of P(OMe)3 and 160 mg of Pd(OAc)2. The reaction mixture was heated for 2 h at 120° C. and the DMF was evaporated under vacuo. The resulting residue was diluted with DCM and filtered over a pad of silica gel. The filtrate was washed with 10%-citric acid, water and brine. The organic phase was dried over anh. Na2SO4 and concentrated in vacuo. The resulting crude material was purified by CC using heptane/EtOAc from 94/6 to 50/50 as eluant to yield 2.7 g of 3-isoquinolin-4-yl-acrylic acid tert.-butyl ester as a yellow solid.

後処理

  1. customthe DMF was evaporated under vacuo
  2. additionThe resulting residue was diluted with DCM
  3. filtrationfiltered over a pad of silica gel
  4. washThe filtrate was washed with 10%-citric acid, water and brine
  5. dry with materialThe organic phase was dried over anh. Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude material was purified by CC

出典と根拠

ORDレコード
ord-0de19a722697466aa16e3b3efa644e10
出典データセット
uspto-grants-2012_06
特許番号
US08202885B2

関連ノート

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