Sodium Carbonate → HCID 59380104, compound

HRID 2353747Notes

Reaction equation

HRID 2353747 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([S:11]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)(=[O:13])=[O:12])([CH3:10])[CH3:9])[CH:5]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][C@@H:23]2[CH3:28])[N:3]=1.CC1(C)C(C)(C)OB([C:37]2[CH:43]=[CH:42][C:40]([NH2:41])=[CH:39][CH:38]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.COCCOC.C(O)C.O.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:21][C:16]1[CH:15]=[C:14]([S:11]([C:8]([C:6]2[CH:5]=[C:4]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][C@@H:23]3[CH3:28])[N:3]=[C:2]([C:37]3[CH:43]=[CH:42][C:40]([NH2:41])=[CH:39][CH:38]=3)[N:7]=2)([CH3:10])[CH3:9])(=[O:13])=[O:12])[CH:19]=[C:18]([F:20])[CH:17]=1

Participants

10

Reactant 3

HCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59380049HCID 59380049, compound

Product 1

HCID 59380104HCID 59380104, compoundYield 94.5%

Reagents, catalysts & solvents 6

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A stream of nitrogen was passed through a mixture of 2-chloro-4-[2-(3,5-difluorophenyl)sulfonylpropan-2-yl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (1.4 g, 3.24 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.923 g, 4.21 mmol) and 2M aqueous sodium carbonate (5.83 mL, 11.67 mmol) in DMF (6 mL), DME (5 mL), ethanol (5 mL) and water (12.5 mL) at RT. The reaction mixture was treated with dichlorobis(triphenylphosphine)palladium(II) (0.114 g, 0.16 mmol) and was stirred at 80° C. for 1 hour. The reaction mixture was diluted with ethyl acetate and washed with water. The organic solution was dried (MgSO4) and concentrated under reduced pressure. The residue was chromatographed on silica, eluting with 25%-60% ethyl acetate in isohexane, to give the desired material as a pale yellow solid (1.496 g).

Workup

  1. washwashed with water
  2. dry with materialThe organic solution was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was chromatographed on silica
  5. washeluting with 25%-60% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-4742ef5a556e412ab2b778db71941afd
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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