Ethanol → HCID 59380005, compound

HRID 2353761Notes

Reaction equation

HRID 2353761 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:15]2[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=2)O1.Cl[C:24]1[N:29]=[C:28]([C:30]([S:33]([C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=2)(=[O:35])=[O:34])([CH3:32])[CH3:31])[CH:27]=[C:26]([N:43]2[CH2:48][CH2:47][O:46][CH2:45][C@@H:44]2[CH3:49])[N:25]=1.C(O)C>COCCOC.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.O.CN(C=O)C>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([S:33]([C:30]([C:28]2[CH:27]=[C:26]([N:43]3[CH2:48][CH2:47][O:46][CH2:45][C@@H:44]3[CH3:49])[N:25]=[C:24]([C:15]3[CH:16]=[CH:17][C:18]([NH2:19])=[CH:20][CH:21]=3)[N:29]=2)([CH3:32])[CH3:31])(=[O:34])=[O:35])=[CH:37][CH:38]=1

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59380097HCID 59380097, compound

Product 1

HCID 59380005HCID 59380005, compoundYield 82.9%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Sodium carbonate (2M in water, 6.69 mL, 13.38 mmol) was added to 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.815 g, 3.72 mmol) and 2-chloro-4-[2-(4-chlorophenyl)sulfonylpropan-2-yl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (1.60 g, 3.72 mmol) in a mixture of DME (10 mL), ethanol (10.00 mL), DMF (10.00 mL) and water (20 mL) at RT under nitrogen. The mixture was degassed and purged with nitrogen three times. Bis(triphenylphosphine)palladium(II) chloride (0.130 g, 0.19 mmol) was added and the mixture was degassed and purged with nitrogen a further three times. The resulting suspension was stirred under nitrogen at 80° C. for 90 minutes. The reaction mixture was concentrated and diluted with ethyl acetate (150 mL) and washed with water (2×150 mL) and saturated brine (100 mL). The organic layer was dried (MgSO4), filtered and evaporated. The crude product was purified by flash silica chromatography, elution gradient 30 to 45% ethyl acetate in isohexane, to give the desired material as a white solid (1.502 g).

Workup

  1. customThe mixture was degassed
  2. custompurged with nitrogen three times
  3. customthe mixture was degassed
  4. custompurged with nitrogen a further three times
  5. concentrationThe reaction mixture was concentrated
  6. additiondiluted with ethyl acetate (150 mL)
  7. washwashed with water (2×150 mL) and saturated brine (100 mL)
  8. dry with materialThe organic layer was dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude product was purified by flash silica chromatography, elution gradient 30 to 45% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-dbd1dd2c9c7640c1add8a515b00ab959
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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