Cesium carbonate → HCID 178458425, compound

HRID 2236861Notes

Reaction equation

HRID 2236861 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH3:26])=[C:19]([OH:27])[CH:18]=1.[O:28]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29]1.C(=O)([O-])[O-].[Cs+].[Cs+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C>C(Cl)Cl.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].CN(C)C=O>[O:28]1[CH:32]=[CH:31][C:30]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/3=[CH:14]\[NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH3:26])=[C:19]([OH:27])[CH:18]=2)=[CH:29]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2734358Furan-3-boronic acidHCID 178458419HCID 178458419, compound

Product 1

HCID 178458425HCID 178458425, compoundYield 8%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(4Z)-6-Bromo-4-{[(3-hydroxy-4-propoxybenzyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione (110 mg, 0.255 mmol) is mixed with 3-furanboronic acid (58 mg, 0.51 mmol), Pd2(dba)3 (35 mg, 0.038 mmol), and cesium carbonate (166 mg, 0.51 mmol). After the solids were degassed, N,N-dimethylformamide (1.7 mL) and P(t-Bu)3 (15.5 mg, 0.077 mmol) were added. The mixture is heated at 100 C for 1 h, diluted with methylene chloride, and filtered. The filtrate is evaporated to dryness and purified by column chromatography to yield 8.5 mg (8%) of the title compound as a white solid. MS (ESI) m/z 417, 419 (M+H)+1

Workup

  1. customAfter the solids were degassed
  2. temperatureThe mixture is heated at 100 C for 1 h
  3. filtrationfiltered
  4. customThe filtrate is evaporated to dryness
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-793c6e5545a443e689499780798f0a5a
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…