Sodium Carbonate → HCID 59380212, compound

HRID 2353749Notes

Reaction equation

HRID 2353749 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][S:9]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=2)(=[O:11])=[O:10])[CH:5]=[C:4]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][C@@H:21]2[CH3:26])[N:3]=1.CC1(C)C(C)(C)OB([C:35]2[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.COCCOC.C(O)C.O.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:19][C:14]1[CH:13]=[C:12]([S:9]([CH2:8][C:6]2[CH:5]=[C:4]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][C@@H:21]3[CH3:26])[N:3]=[C:2]([C:35]3[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=3)[N:7]=2)(=[O:11])=[O:10])[CH:17]=[C:16]([F:18])[CH:15]=1

Participants

9

Reactant 3

HCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 59380209HCID 59380209, compound

Product 1

HCID 59380212HCID 59380212, compoundYield 88.7%

Reagents, catalysts & solvents 5

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A stream of nitrogen was passed through 2-chloro-4-[(3,5-difluorophenyl)sulfonylmethyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (0.727 g, 1.8 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.513 g, 2.34 mmol) and 2M aqueous sodium carbonate (3.24 mL, 6.48 mmol) in DMF (3.75 mL), DME (5 mL), ethanol (5 mL) and water (12.5 mL) for 15 minutes. The reaction mixture was treated with dichlorobis(triphenylphosphine)palladium(II) (0.063 g, 0.09 mmol) and the mixture was stirred at 80° C. for 16 hours. The mixture was partitioned between ethyl acetate and 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 product as a yellow solid (0.735 g).

Workup

  1. customThe mixture was partitioned between ethyl acetate and 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-704c6b1b46324a2fa831415549e80c55
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

Loading…