Cesium carbonate → HCID 67262142, compound

HRID 410409Notes

Reaction equation

HRID 410409 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([NH:19][C:20]3[N:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][N:21]=3)[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])O1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:72]1[S:76][CH:75]=[N:74][CH:73]=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[S:76]1[C:72]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([NH:19][C:20]3[N:25]=[C:24]([C:26]([F:29])([F:27])[F:28])[CH:23]=[CH:22][N:21]=3)[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:73][N:74]=[CH:75]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 5460595-BromothiazoleHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67433486Methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}benzoate

Product 1

HCID 67262142HCID 67262142, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a flask containing the product of Step 2 (391 mg, 0.92 mmol), dicyclohexyl[2′,4′,6′-tri(propan-2-yl)biphenyl-2-yl]phosphane (44 mg, 0.092 mmol), Pd2(dba)3 (42 mg, 0.046 mmol), cesium carbonate (602 mg, 1.85 mmol) was added a solution of 5-bromothiazole in a degassed mixture of dioxane (8.4 mL) and water (840 μL). The solution was evacuated and then purged with argon 5 times and then heated at 90° C. overnight. The reaction was cooled, diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated. Flash chromatography was used for purification to yield methyl 3-(1,3-thiazol-5-yl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}benzoate (254 mg, 0.67 mmol, 72% yield). MS ESI: [M+H]+ m/z 381.0.

Workup

  1. customThe solution was evacuated
  2. custompurged with argon 5 times
  3. temperatureThe reaction was cooled
  4. additiondiluted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customFlash chromatography was used for purification

Sources & evidence

ORD record
ord-79ed51a88cc44ae08a6a751b14a0d053
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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