Potassium Carbonate → HCID 22063520, compound

HRID 1828520Notes

Reaction equation

HRID 1828520 reaction equation
FC(F)(F)S(O[C:7]1[N:8]=[C:9]2[CH:17]=[C:16]([CH2:18][CH2:19][C:20]3[S:21][CH:22]=[C:23]([CH:25]([CH3:27])[CH3:26])[N:24]=3)[CH:15]=[CH:14][N:10]2[C:11](=[O:13])[CH:12]=1)(=O)=O.B1([C:36]2[CH:41]=[CH:40][CH:39]=[N:38][CH:37]=2)OCCCO1.[Br-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O1CCOCC1>[CH:25]([C:23]1[N:24]=[C:20]([CH2:19][CH2:18][C:16]2[CH:15]=[CH:14][N:10]3[C:11](=[O:13])[CH:12]=[C:7]([C:36]4[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=4)[N:8]=[C:9]3[CH:17]=2)[S:21][CH:22]=1)([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 253877Potassium BromideHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 22063530HCID 22063530, compound

Product 1

HCID 22063520HCID 22063520, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

2-Trifluoromethanesulfonyloxy-8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4H-pyrido[1,2-a]pyrimidin-4-one(499 mg), pyridine-3-boronic acid 1,3-propanediol cyclic ester (364 mg), palladium tetrakistriphenylphosphine (65 mg), potassium bromide (146 mg) and potassium carbonate (231 mg) were added with dioxane(8 ml) and stirred overnight at 85° C. under nitrogen atmosphere. The reaction mixture was cooled and then added with ethyl acetate. Insoluble solids were removed by filtration, and the solvent of the filtrate was evaporated. The residue was purified by silica gel column chromatography to obtain the title compound (400 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customInsoluble solids were removed by filtration
  3. customthe solvent of the filtrate was evaporated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-96336f0bead84cdda9b9dd673767ca05
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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