Cesium carbonate → HCID 86606578, compound

HRID 2244458Notes

Reaction equation

HRID 2244458 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([NH:9][C:10]([C:12]2[N:13]=[C:14]([CH3:18])[S:15][C:16]=2Br)=[O:11])[CH:6]=[CH:5][N:4]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.[F:61][C:62]1[CH:63]=[C:64]([CH:66]=[C:67]([F:69])[CH:68]=1)[NH2:65].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O1CCOCC1>[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([NH:9][C:10]([C:12]2[N:13]=[C:14]([CH3:18])[S:15][C:16]=2[NH:65][C:64]2[CH:63]=[C:62]([F:61])[CH:68]=[C:67]([F:69])[CH:66]=2)=[O:11])[CH:6]=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 965953,5-DifluoroanilineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86606579HCID 86606579, compound

Product 1

HCID 86606578HCID 86606578, compoundYield 8.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

A microwave vial was charged with 5-bromo-2-methyl-thiazole-4-carboxylic acid (2-hydroxymethyl-pyridin-4-yl)-amide (0.135 g, 0.411 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (0.81 g, 0.140 mmol) and palladium dibenzylideneacetone (Pd2dba3)-chloroform complex (0.044 g, 0.043 mmol). Degassed dioxane (10 ml) was added, followed by 3,5-difluoroaniline (0.064 g, 0.496 mmol) and cesium carbonate (0.271 g, 0.831 mmol) The vial was then irradiated in a microwave oven at 150° C. for 40 min. The mixture was diluted with THF and the solids filtered, washing with THF. The filtrate was evaporated and the residue purified by flash chromatography on silica gel with dichloromethane/methanol 100:0→90:10 gradient to yield the title compound (0.013 g, 8%) as an off-white solid, MS (ISP): m/e=377.4 (M+H+).

Workup

  1. customwas then irradiated in a microwave oven at 150° C. for 40 min
  2. filtrationthe solids filtered
  3. washwashing with THF
  4. customThe filtrate was evaporated
  5. customthe residue purified by flash chromatography on silica gel with dichloromethane/methanol 100:0→90:10 gradient

Sources & evidence

ORD record
ord-244231b3463a44f6a902e2fca15aebbf
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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