Dimethylformamide → HCID 59380082, compound

HRID 2353738Notes

Reaction equation

HRID 2353738 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[CH3:14])[CH:5]=[C:4]([C:15]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])(=[O:20])=[O:19])([CH3:17])[CH3:16])[N:3]=1.CC1(C)C(C)(C)OB([C:39]2[CH:45]=[CH:44][C:42]([NH2:43])=[CH:41][CH:40]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>C(O)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.COCCOC.O>[CH3:14][C@H:9]1[CH2:10][O:11][CH2:12][CH2:13][N:8]1[C:6]1[CH:5]=[C:4]([C:15]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])(=[O:20])=[O:19])([CH3:17])[CH3:16])[N:3]=[C:2]([C:39]2[CH:45]=[CH:44][C:42]([NH2:43])=[CH:41][CH:40]=2)[N:7]=1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59380175HCID 59380175, compound

Product 1

HCID 59380082HCID 59380082, compoundYield 69.9%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
95 °C

Procedure

Bis(triphenylphosphine)palladium(II) chloride (200 mg, 0.28 mmol) was added to 2-chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-[2-[2-(trifluoromethyl)phenyl]sulfonylpropan-2-yl]pyrimidine (1.91 g, 4.12 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.353 g, 6.18 mmol) and sodium carbonate (10 mL, 20.00 mmol) in a mixture of ethanol (5 mL), DMF (10 mL), water (7 mL) and DME (25 mL) at RT. The resulting mixture was degassed then stirred at 95° C. for 18 hours. The reaction mixture was allowed to cool and diluted with ethyl acetate (200 mL), and washed with water (2×200 mL), and brine (100 mL). The organic layer was dried (Na2SO4), filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 10 to 60% ethyl acetate in isohexane, and the resultant material triturated with a mixture of diethyl ether and isohexane to give the desired material as a white solid (1.50 g).

Workup

  1. customThe resulting mixture was degassed
  2. temperatureto cool
  3. additiondiluted with ethyl acetate (200 mL)
  4. washwashed with water (2×200 mL), and brine (100 mL)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto afford crude product
  9. customThe crude product was purified by flash silica chromatography, elution gradient 10 to 60% ethyl acetate in isohexane
  10. customthe resultant material triturated with a mixture of diethyl ether and isohexane

Sources & evidence

ORD record
ord-cfac0267c9024b87957700268d6d674e
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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