Dimethylformamide → HCID 69437141, compound

HRID 347325Notes

Reaction equation

HRID 347325 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[C:22]3[O:21][CH:20]=[CH:19][C:18]=3[C:17](I)=[CH:16][CH:15]=1)=[CH:10][C:9]([O:24][CH3:25])=[C:8]([O:26][CH3:27])[CH:7]=2)#[N:2].CN(C)[CH:30]=[O:31]>>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[C:22]3[O:21][CH:20]=[CH:19][C:18]=3[C:17]([CH:18]=[CH:19][C:20]([O:31][CH3:30])=[O:21])=[CH:16][CH:15]=1)=[CH:10][C:9]([O:24][CH3:25])=[C:8]([O:26][CH3:27])[CH:7]=2)#[N:2]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 11612524HCID 11612524, compound

Product 1

HCID 69437141HCID 69437141, compound

Conditions

Temperature
115 °C

Procedure

The 3-cyano-6,7-dimethoxy-4-(4-iodobenzofuran-7-ylamino)quinoline (0.275 g) was suspended in N,N-dimethylformamide (15 ml) in a nitrogen-flushed vessel, then palladium (II) acetate (16 mg) was added, followed by methyl acrylate (1.1 ml) and triethylamine (0.6 ml). The reaction was heated to 115° C. for 5 hours before filtration and evaporation of solvents under reduced pressure. The residue was purified by column chromatography on silica using increasingly polar mixtures of iso-hexane with ethyl acetate as eluent The resulting product was triturated with diethyl ether and filtered. There was thus obtained the title compound (0.203 g), as a yellow solid; NMR Spectrum: (DMSOd6) 3.77 (s, 3H), 3.94 (s, 3H), 3.99 (s, 3H), 6.73 (d, 1H), 7.31 (d, 1H), 7.40(s, 1H), 7.47 (d, 1H), 7.76 (d, 1H), 7.86 (s, 1H), 7.97 (d, 1H), 8.08 (d, 1H), 8.56 (s, 1H), 10.02 (br s, 1H); Mass Spectrum: M+H+ 430.

Workup

  1. customflushed vessel
  2. additionpalladium (II) acetate (16 mg) was added
  3. customThe residue was purified by column chromatography on silica using
  4. temperatureincreasingly polar mixtures of iso-hexane with ethyl acetate as eluent The resulting product
  5. customwas triturated with diethyl ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-e9952a0ca856428eb77c4e4b7fb9f88e
Source dataset
uspto-grants-2007_02
Patent number
US07173136B2

Reaction notes

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