Toluene → HCID 15411600, compound

HRID 1415697Notes

Reaction equation

[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:13]2=[N:14][C:15]3[C:20]([C:21](=[O:22])[N:12]2[CH:11]=[CH:10][CH:9]=1)=[CH:19][C:18](I)=[CH:17][CH:16]=3)=[O:7].[N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[C:27](B(O)O)[CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>O>[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:13]2=[N:14][C:15]3[C:20]([C:21](=[O:22])[N:12]2[CH:11]=[CH:10][CH:9]=1)=[CH:19][C:18]([C:27]1[CH:26]=[N:25][C:34]2[C:29]([CH:28]=1)=[CH:30][CH:31]=[CH:32][CH:33]=2)=[CH:17][CH:16]=3)=[O:7]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of N-[2-(dimethylamino)ethyl]-2-iodo-11-oxo-11H-pyrido[2,1-b]quinazoline-6-carboxamide (750 mg), 3-quinolinylboronic acid (743.47 mg), tetrakis-(triphenylphosphine)palladium(0) (198.67 mg) and sodium carbonate (4.3 ml of 2 M (8.6 mmol))and 33 ml of toluene was heated at 120° C. for 7 hours and cooled to room temperature. The reaction mixture was diluted with 70 ml of water and extracted with 3×70 ml CHCl3. The organic layer was dried over Na2SO4 and evaporated in vacuo to a residue. The residue was purified by column chroma-tography on silica gel by elution with 5-10% MeOH/CHCl3 to give 501 mg of a yellow solid.

Workup

temperaturecooled to room temperature
extractionextracted with 3×70 ml CHCl3
dry with materialThe organic layer was dried over Na2SO4
customevaporated in vacuo to a residue
customThe residue was purified by column chroma-tography on silica gel by elution with 5-10% MeOH/CHCl3

Sources & evidence

ORD record: ord-8ce5c43907234072a0cc2b21e4c414a4
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05908840

Reaction notes

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