Sodium Carbonate → HCID 59242791, compound

HRID 1514415Notes

Reaction equation

HRID 1514415 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[F:10][C:11]1([F:23])[O:15][C:14]2[CH:16]=[CH:17][CH:18]=[C:19](B(O)O)[C:13]=2[O:12]1.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:23][C:11]1([F:10])[O:12][C:13]2[CH:19]=[CH:18][CH:17]=[C:16]([C:2]3[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=3)[C:14]=2[O:15]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 38589014-Iodo-2-(methylthio)pyrimidineHCID 16427145(2,2-Difluoro-1,3-dioxaindan-4-yl)boronic acid

Product 1

HCID 59242791HCID 59242791, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

4-Iodo-2-methylsulfanyl-pyrimidine (453 mg, 1.79 mmol), 2,2-difluoro-benzo[1,3]dioxole-4-boronic acid (727 mg, 3.59 mmol), Na2CO3 (380 mg, 3.59 mmol), 2-(dicyclohexylphosphino)biphenyl (125 mg, 0.36 mmol) were suspended in degassed DME-water solution (5-1, 6.5 ml). After bubbling N2 into the mixture for 20 minutes, Pd(PPh3)4 (413 mg, 0.36 mmol) was added and the mixture was stirred at 90° C. for 3 hours. The solvent was evaporated under vacuum and the crude was dissolved in DCM and washed with water and brine. The organic phase was dried (Na2SO4) and evaporated; the crude was purified by flash chromatography with hexane-ethyl acetate (8-2) to give the title compound (326 mg, 65% yield).

Workup

  1. customAfter bubbling N2 into the mixture for 20 minutes
  2. customThe solvent was evaporated under vacuum
  3. dissolutionthe crude was dissolved in DCM
  4. washwashed with water and brine
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated
  7. customthe crude was purified by flash chromatography with hexane-ethyl acetate (8-2)

Sources & evidence

ORD record
ord-d616c864de42473f993dffb2f38b60af
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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