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

HRID 220264

Reaktionsgleichung

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]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-0de19a722697466aa16e3b3efa644e10
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08202885B2

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