1-Ethenyl-4-methylbenzene → HCID 178424838, compound

HRID 2185187Notes

Reaction equation

HRID 2185187 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:19]=[C:18]([OH:20])[C:17]3[C:12](=[C:13](I)[CH:14]=[C:15]([F:21])[CH:16]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[CH2:29])=[CH:26][CH:25]=1.C(N(C(C)C)CC)(C)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:23][C:24]1[CH:31]=[CH:30][C:27](/[CH:28]=[CH:29]/[C:13]2[CH:14]=[C:15]([F:21])[CH:16]=[C:17]3[C:12]=2[N:11]=[C:10]([NH:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[N:19]=[C:18]3[OH:20])=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 121611-Ethenyl-4-methylbenzeneHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 178518006HCID 178518006, compound

Product 1

HCID 178424838HCID 178424838, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-((3,4-dichlorophenyl)amino)-6-fluoro-8-iodoquinazolin-4-ol (45 mg) and palladium acetate (13.5 mg) in dimethylformamide (1.3 mL) was added 4-methylstyrene (26 μL), diisopropylethylamine (200 μL) and tri-o-tolylphosphine (12 mg). The resulting mixture was heated at 120° C. for 3 h. The mixture was then cooled to room temperature and the supernatant was removed by pipette from the settled black solids. The solvent and the excess volatile reagents were removed in vacuo, providing the crude product as a brown solid. This residue was triturated with 50% (v/v) methanol/dichloromethane (3 mL) and the resulting yellow solid was dried in vacuo to afford the title compound (25.1 mg). 1H NMR (300 MHz, DMSO-d6): δ11.24 (brs, 1H), 9.12 (brs, 1H), 8.59 (d, J=2.4 Hz, 1H), 8.04 (dd, J=3 & 10.2 Hz, 1H), 7.91 (d, J=16.8 Hz, 1H), 7.62-7.56 (m, 4H), 7.47 (d, J=16.8 Hz, 1H), 7.36 (dd, J=2.4 & 9 Hz, 1H), 7.31 (d, J=6 Hz, 2H), 2.34 (s, 3H). MS (APCI+): m/z 440.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. customthe supernatant was removed by pipette from the settled black solids
  3. customThe solvent and the excess volatile reagents were removed in vacuo
  4. customproviding the crude product as a brown solid
  5. customThis residue was triturated with 50% (v/v) methanol/dichloromethane (3 mL)
  6. customthe resulting yellow solid was dried in vacuo

Sources & evidence

ORD record
ord-6a116cc7c10d4f6d85ed6749502c14f5
Source dataset
uspto-grants-2002_06
Patent number
US06399603B1

Reaction notes

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