4-Vinylbenzoic acid → HCID 178524342, compound

HRID 2185183Notes

Reaction equation

HRID 2185183 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](Br)[CH:14]=[C:15]([N+:21]([O-:23])=[O:22])[CH:16]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:25]([C:27]1[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=1)=[CH2:26].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)C(C)C)(C)C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[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](/[CH:26]=[CH:25]/[C:27]4[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=4)[CH:14]=[C:15]([N+:21]([O-:23])=[O:22])[CH:16]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 140984-Vinylbenzoic acidHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 178526426HCID 178526426, compound

Product 1

HCID 178524342HCID 178524342, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-((3,4-dichlorophenyl)amino)-8-bromo-6-nitroquinazolin-4-ol (50 mg) in N,N-dimethylformamide (2 mL) was added 4-vinylbenzoic acid (35 mg), followed by palladium acetate (2.6 mg), tri-o-tolylphosphine (7.1 mg) and N,N-diisopropylethylamine (0.24 mL). The reaction mixture was heated at 120° C. for 24 h, then was cooled to room temperature and concentrated in vacuo. The residue was triturated with 50% (v/v) methanol/dichloromethane (2 mL). The resulting solid was isolated by filtration, washed sequentially with diethyl ether and water, then was dried in vacuo to give the title compound (36 mg). 1H NMR (300 MHz, DMSO-d6/CF3CO2H) δ8.75 (d, J=2.7 Hz, 1H), 8.60 (d, J=2.7 Hz, 1H), 8.43 (d, J=4.5 Hz, 1H), 7.99-7.88 (m, 3H), 7.74 (d, J=8.4 Hz, 1H), 7.67-7.51 (m, 2H), 7.38 (dd, J=8.7, 2.6 Hz, 1H). HPLC Method B 8.26 min. MS (APCI−) m/z 496, 498.

Workup

  1. temperaturewas cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was triturated with 50% (v/v) methanol/dichloromethane (2 mL)
  4. customThe resulting solid was isolated by filtration
  5. washwashed sequentially with diethyl ether and water
  6. customwas dried in vacuo

Sources & evidence

ORD record
ord-2530487c1d4a4e1e964cea1ee2fb7dd5
Source dataset
uspto-grants-2002_06
Patent number
US06399603B1

Reaction notes

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