Sodium Carbonate → HCID 59379908, compound

HRID 2353725Notes

Reaction equation

HRID 2353725 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)O1.Cl[C:18]1[N:23]=[C:22]([CH2:24][S:25]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)(=[O:27])=[O:26])[CH:21]=[C:20]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][C@@H:36]2[CH3:41])[N:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.COCCOC.O.C(O)C.C(OCC)(=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>[F:34][C:31]1[CH:32]=[CH:33][C:28]([S:25]([CH2:24][C:22]2[CH:21]=[C:20]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][C@@H:36]3[CH3:41])[N:19]=[C:18]([C:9]3[CH:10]=[CH:11][C:12]([NH2:13])=[CH:14][CH:15]=3)[N:23]=2)(=[O:27])=[O:26])=[CH:29][CH:30]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59380058HCID 59380058, compound

Product 1

HCID 59379908HCID 59379908, compoundYield 97%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
90 °C

Procedure

Dichlorobis(triphenylphosphine)palladium(II) (136 mg, 0.19 mmol) was added to 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.107 g, 5.05 mmol) and 2-chloro-4-[(4-fluorophenyl)sulfonylmethyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (1.50 g, 3.89 mmol) and sodium carbonate (5 mL, 10.00 mmol) in 18% DMF in DME:water:ethanol (7:3:2) (20 mL). The resulting solution was stirred at 90° C. for 4 hours. The reaction mixture was diluted with ethyl acetate (20 mL), and washed with water (2×20 mL). The organic layer was dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 5 to 60% ethyl acetate in isohexane, to give the desired material as a cream solid (1.670 g).

Workup

  1. washwashed with water (2×20 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto afford crude product
  6. customThe crude product was purified by flash silica chromatography, elution gradient 5 to 60% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-75198425d42745a8901d1ac64b539dae
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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