Cesium carbonate → HCID 85472925, compound

HRID 1850703Notes

Reaction equation

HRID 1850703 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([NH:14][C:15]2[S:19][N:18]=[C:17]([CH3:20])[C:16]=2Br)=[O:13])=[C:5]2[N:6]=[CH:7][C:8]([F:10])=[CH:9][N:4]2[N:3]=1.CN([C:25](ON1N=NC2C=CC=CC1=2)=[N+:26]([CH3:28])[CH3:27])C.[B-](F)(F)(F)F.[C:44](=[O:47])([O-])[O-].[Cs+].[Cs+].[CH:50]1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>O1CCOCC1.[Pd+2].O>[NH2:1][C:2]1[C:11]([C:12]([NH:14][C:15]2[S:19][N:18]=[C:17]([CH3:20])[C:16]=2[CH2:27][N:26]2[CH2:25][CH2:44][O:47][CH2:50][CH2:28]2)=[O:13])=[C:5]2[N:6]=[CH:7][C:8]([F:10])=[CH:9][N:4]2[N:3]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 90411776HCID 90411776, compound

Product 1

HCID 85472925HCID 85472925, compound

Reagents, catalysts & solvents 3

HCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2-amino-N-(4-bromo-3-methyl-isothiazol-5-yl)-6-fluoro-pyrazolo[1,5-a]pyrimidine-3-carboxamide (50 mg, 0.1078 mmol), trifluoro(morpholinomethyl)boranuide (Potassium Ion (1)) (29.01 mg, 0.1401 mmol), dicesium carbonate (105.4 mg, 0.3234 mmol), palladium(+2) cation diacetate (4.84 mg, 0.02156 mmol), dicyclohexyl-[2-(2,4,6-triisopropylphenyl)phenyl]phosphane (20.56 mg, 0.04312 mmol) in dioxane (4 mL)-water (0.5 mL) was heated at 90° C. for 5 h. The reaction mixture was concentrated in vacuo and the residue was purified by fractionlynx. The clean fractions were freeze dried, yielding 2-amino-6-fluoro-N-(3-methyl-4-(morpholinomethyl)isothiazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide as a pale yellow solid. (21 mg, 32%). MS (ES+) 392.2.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by fractionlynx
  3. customdried

Sources & evidence

ORD record
ord-f716f370e63b40f19859031804cc8382
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

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