Cesium carbonate → HCID 10298349, compound

HRID 896081Notes

Reaction equation

HRID 896081 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:12][CH:11]=2)=[O:9])[CH:7]=1.[CH2:27]([N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)[C:28]#[CH:29].C([O-])([O-])=O.[Cs+].[Cs+].C(N(CC)C(C)C)(C)C>COCCOCCOC.CC(OC)(C)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[NH:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]([C:6]2[CH:7]=[C:2]([C:29]#[C:28][CH2:27][N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[CH:3]=[CH:4][C:5]=2[O:25][CH3:26])=[O:9])=[CH:11][CH:12]=1

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 81531DiisopropylethylamineHCID 4129414-(2-Propyn-1-yl)morpholineHCID 22349575(5-Bromo-2-methoxy-phenyl)-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Product 1

HCID 10298349HCID 10298349, compoundYield 40.6%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8150DiglymeSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

(5-Bromo-2-methoxy-phenyl)-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone (1.00 g; 2.37 mmol), 4-prop-2-ynyl-morpholine (1.2 g; 9.5 mmol) PdCl2(PPh3)2 (320 mg; 0.4 mmol), Cs2CO3 (2.0 g; 6.2 mmol) and CuI (100 mg; 0.52 mmol) are dissolved in diethylene glycol dimethyl ether (10 ml) and N,N-diisopropylethylamine (5 ml) and heated to 140° C. for 1 hour. The reaction mixture is diluted with TBME, filtered, evaporated and purified by chromatography (SiO2, acetone/hexanes 3/7>6/4) to yield the title compound as yellow foam (445 mg; 40%).

Workup

  1. filtrationfiltered
  2. customevaporated
  3. custompurified by chromatography (SiO2, acetone/hexanes 3/7>6/4)

Sources & evidence

ORD record
ord-0cbd79874dbe40ba928a5db18c6ee96c
Source dataset
uspto-grants-2005_07
Patent number
US06919336B2

Reaction notes

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