Hexane → HCID 118473740, compound

HRID 2205082Notes

Reaction equation

HRID 2205082 reaction equation
FC(F)(F)S(O[C:7]1[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:10]2[N:11]=[C:12]([C:19]([F:22])([F:21])[F:20])[CH:13]=[C:14]([C:15]([F:18])([F:17])[F:16])[N:9]2[N:8]=1)(=O)=O.[C:32]([O:36][C:37]([NH:39][C:40]1([C:44]2[CH:49]=[CH:48][C:47](B(O)O)=[CH:46][CH:45]=2)[CH2:43][CH2:42][CH2:41]1)=[O:38])([CH3:35])([CH3:34])[CH3:33].C(=O)([O-])[O-].[Cs+].[Cs+].CCCCCC>CN(C=O)C>[C:24]1([C:23]2[C:7]([C:47]3[CH:48]=[CH:49][C:44]([C:40]4([NH:39][C:37](=[O:38])[O:36][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:43][CH2:42][CH2:41]4)=[CH:45][CH:46]=3)=[N:8][N:9]3[C:14]([C:15]([F:16])([F:17])[F:18])=[CH:13][C:12]([C:19]([F:20])([F:21])[F:22])=[N:11][C:10]=23)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 10796Cesium carbonateHCID 89689535HCID 89689535, compoundHCID 123959447HCID 123959447, compound

Product 1

HCID 118473740HCID 118473740, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

3-Phenyl-5,7-bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-2-yl trifluoromethanesulfonate (230 mg, 0.46 mmol, 1 eq), (4-{1-[(tert-butoxycarbonyl)amino]cyclobutyl}-phenyl)boronic acid [Int-2A] (210 mg, 0.68 mmol, 85% purity, 1.5 eq), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (40.8 mg, 0.05 mmol, 0.11 eq) and cesium carbonate (371 mg, 1.14 mmol, 2.5 eq) were dissolved in 3.8 mL DMF and heated under microwave irradiation to a temperature of 110° C. After a hold time of 35 sec the reaction mixture was cooled to it and the volatile components were removed in vacuo. The resulting crude material was purified by preparative MPLC [Biotage Isolera: SNAP cartridge 25 g, hexane→hexane/ethyl acetate (2/1)] to yield a sample of insufficient purity. This was forwarded to another preparative MPLC with adapted gradient [Biotage Isolera: SNAP cartridge 25 g, hexane→hexane/ethyl acetate (4/1)] to give 160 mg (55%) of title compound in 90% purity (UPLC, area-%).

Workup

  1. temperatureAfter a hold time of 35 sec the reaction mixture was cooled to it
  2. customthe volatile components were removed in vacuo
  3. customThe resulting crude material was purified by preparative MPLC [Biotage Isolera: SNAP cartridge 25 g, hexane→hexane/ethyl acetate (2/1)]
  4. customto yield a sample of insufficient purity

Sources & evidence

ORD record
ord-ba71919f78294ed8a1871782720e44d6
Source dataset
uspto-grants-2016_06
Patent number
US09370517B2

Reaction notes

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