Triethylamine → (Z)-ethyl 2-(6,7-dimethoxy-1-oxo-2,3-dihydroisoquinolin-4(1H)-ylidene)acetate

HRID 2175715Notes

Reaction equation

HRID 2175715 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC.I[C:28]1[CH:44]=[C:43]([O:45][CH3:46])[C:42]([O:47][CH3:48])=[CH:41][C:29]=1[C:30]([NH:32][CH2:33]/[CH:34]=[CH:35]\[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[O:31]>CC#N.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:46][O:45][C:43]1[CH:44]=[C:28]2[C:29](=[CH:41][C:42]=1[O:47][CH3:48])[C:30](=[O:31])[NH:32][CH2:33]/[C:34]/2=[CH:35]\[C:36]([O:38][CH2:39][CH3:40])=[O:37]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 70935552(Z)-ethyl 4-(2-iodo-4,5-dimethoxybenzamido)but-2-enoate

Product 1

HCID 86672723(Z)-ethyl 2-(6,7-dimethoxy-1-oxo-2,3-dihydroisoquinolin-4(1H)-ylidene)acetateYield 83.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A stirred solution of Pd(OAc)2 (16 mg, 0.07 mmol), PPh3 (61 mg, 0.23 mmol), Et3N (0.58 mL, 4.2 mmol) and (Z)-ethyl 4-(2-iodo-4,5-dimethoxybenzamido)but-2-enoate (860 mg, 2.1 mmol) in dry CH3CN (20 mL) was heated at 70° C. overnight under an argon atmosphere. The reaction was allowed to cool to room temperature and then concentrated under reduced pressure. The residue was purified by flash chromatography using DCM/MeOH 100:1 (v:v) as eluent to give (Z)-ethyl 2-(6,7-dimethoxy-1-oxo-2,3-dihydroisoquinolin-4(1H)-ylidene)acetate (510 mg, 83%). LC-MS (ES-API); rt 7.56 min; m/z calculated for C15H17NO5 [M+H]+ 292.1, found 292.1.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ca64e2c803a34e0ca1017c186a7adc40
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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