Cesium carbonate → HCID 53628419, compound

HRID 2388893Notes

Reaction equation

HRID 2388893 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=2[F:19])[N:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].[N:60]1([CH:65]2[CH2:70][CH2:69][N:68]([S:71]([NH2:74])(=[O:73])=[O:72])[CH2:67][CH2:66]2)[CH2:64][CH2:63][CH2:62][CH2:61]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:19][C:13]1[C:14]([F:18])=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][S:10][C:4]1[N:3]=[C:2]([NH:74][S:71]([N:68]2[CH2:67][CH2:66][CH:65]([N:60]3[CH2:61][CH2:62][CH2:63][CH2:64]3)[CH2:70][CH2:69]2)(=[O:72])=[O:73])[CH:7]=[C:6]([O:8][CH3:9])[N:5]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 53628420HCID 53628420, compoundHCID 866198774-Chloro-2-([(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine

Product 1

HCID 53628419HCID 53628419, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

The title compound was prepared according to the procedure outlined in example 129 using 4-Chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine (the product of example step i) (0.3 g), tris(dibenzylideneacetone)-dipalladium (0) (20 mg), 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (XPHOS) (15 mg), cesium carbonate (0.70 g) and 4-pyrrolidin-1-ylpiperidine-1-sulfonamide (the product from step i), (0.4 g). The resulting crude material was purified using silica gel chromatography eluting with 5% methanol in DCM and trituration with Et2O to give the title compound as a white solid.

Workup

  1. customThe title compound was prepared
  2. customThe resulting crude material was purified
  3. washeluting with 5% methanol in DCM and trituration with Et2O

Sources & evidence

ORD record
ord-ca9af009fe974bbfbc512f163bc0ea52
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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