4-Vinylpyridine → HCID 178424552, compound

HRID 2185186Notes

Reaction equation

HRID 2185186 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]([CH3:24])[C:16]=3[N+:21]([O-:23])=[O:22])[N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:26]([C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1)=[CH2:27].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>[N:31]1[CH:32]=[CH:33][C:28](/[CH:26]=[CH:27]/[C:13]2[CH:14]=[C:15]([CH3:24])[C:16]([N+:21]([O-:23])=[O:22])=[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:29][CH:30]=1

Participants

7

Reactant 4

HCID 75024-VinylpyridineHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 178422419HCID 178422419, compound

Product 1

HCID 178424552HCID 178424552, compound

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-methyl-5-nitroquinazolin-4-ol (65 mg) in N,N-dimethylformamide (2 mL) was added 4-vinylpyridine (0.040 mL), followed by palladium acetate (14 mg), tri-o-tolylphosphine (30 mg) and N,N-diisopropylethylamine (0.44 mL). The mixture was heated at 120° C. for 22.5 h, then was cooled to room temperature. The supernatant was concentrated in vacuo to a dark oil which was triturated with a 50% (v/v) methanol/dichloromethane (5 mL). The solid product was isolated by filtration, washed with 50% (v/v) methanol/dichloromethane (5 mL) and dried to give the title compound (12 mg). 1H NMR (300 MHz, DMSO-d6) δ11.55 (s, 1H), 9.23, 8.59 (d, J=4.5 Hz, 2H), 8.43 (d, J=2.4 Hz, 1H), 8.21 (s, 1H), 8.08 (d, J=16.8 Hz, 1H), 7.62-7.31 (m, 5H), 2.26 (s, 3H). HPLC (Method B) 9.3 min. MS (APCI+): m/z 468.

Workup

  1. temperaturewas cooled to room temperature
  2. concentrationThe supernatant was concentrated in vacuo to a dark oil which
  3. customwas triturated with a 50% (v/v) methanol/dichloromethane (5 mL)
  4. customThe solid product was isolated by filtration
  5. washwashed with 50% (v/v) methanol/dichloromethane (5 mL)
  6. customdried

Sources & evidence

ORD record
ord-8e4677d2d54c4df1a8fa1cc9230ae39d
Source dataset
uspto-grants-2002_06
Patent number
US06399603B1

Reaction notes

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