Sodium Carbonate → HCID 22598379, compound

HRID 1760346Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[CH:6]=[C:5]2[NH:19][CH3:20].[Cl:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[C:26]([Cl:28])[CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN1CCCC1=O.O.CO.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:21][C:22]1[CH:23]=[C:24]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH:6]=[C:5]3[NH:19][CH3:20])[CH:25]=[C:26]([Cl:28])[CH:27]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To 0.4 g. (1.2 mmole) of N-[6-bromo-2-(3-fluorophenyl)4-quinolinyl]-N-methylamine was added 0.275 g. (1.45 mmole) of 3,5-dichlorophenylboronic acid and a catalytic amount of tris(dibenzylideneacetone)dipalladium (0), 0.0109 g. (0.012 mmole). The mixture was dissolved in 7 mL of N-methyl-2-pyrrolidinone. Sodium carbonate, 0.105 g. (1.45 mmole) was dissolved in a minimal amount of water and added in one portion to the N-methyl-2-pyrrolidinone reaction solution. The mixture was heated to 80° C. for 10 hours. After cooling to room temperature, the mixture was diluted to 10 mL total volume with methanol and filtered through a silica plug. The title compound was isolated by reverse phase HPLC on a 2 inch Dynamax phenyl column using a solvent gradient from 85:15 methanol:water to 100% methanol, yield 0.320 g. (67%).

Workup

temperatureAfter cooling to room temperature
filtrationfiltered through a silica plug

Sources & evidence

ORD record: ord-1993b9881ecc4c698e3a6a2db9a19b71
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06841680B2

Reaction notes

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