Cesium carbonate → HCID 86627642, compound

HRID 604692Notes

Reaction equation

HRID 604692 reaction equation
FC(F)(F)S(O[C:7]1[C:12]([CH2:13][N:14]2[C@@H:18]([CH3:19])[C@@H:17]([C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=3)[O:16][C:15]2=[O:34])=[N:11][CH:10]=[CH:9][N:8]=1)(=O)=O.[Cl:37][C:38]1[CH:39]=[CH:40][C:41]([F:47])=[C:42](B(O)O)[CH:43]=1.C([O-])([O-])=O.[Cs+].[Cs+]>ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCOCC1>[F:29][C:26]([F:27])([F:28])[C:24]1[CH:25]=[C:20]([C@H:17]2[O:16][C:15](=[O:34])[N:14]([CH2:13][C:12]3[C:7]([C:42]4[CH:43]=[C:38]([Cl:37])[CH:39]=[CH:40][C:41]=4[F:47])=[N:8][CH:9]=[CH:10][N:11]=3)[C@H:18]2[CH3:19])[CH:21]=[C:22]([C:30]([F:31])([F:32])[F:33])[CH:23]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 3718925(5-Chloro-2-fluoro-phenyl)boronic acidHCID 86627641HCID 86627641, compound

Product 1

HCID 86627642HCID 86627642, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

3-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)pyrazin-2-yl trifluoromethanesulfonate (Step D, 80 mg, 0.145 mmol), (5-chloro-2-fluorophenyl)boronic acid (30.3 mg, 0.173 mmol), Cs2CO3 (118 mg, 0.361 mmol), 1,1′-bis(diphenylphosphino) ferrocene-palladium dichloride dichloromethane adduct (11.81 mg, 0.014 mmol) and 1,4-dioxane (1 mL) were sealed in a microwave vessel and subjected to microwave irradiation at 140° C. for 25 min. LCMS indicated formation of the desired product. The crude mixture was diluted with MeCN and filtered. The filtrate was purified by preparative HPLC (Kromasil 100-5C 18, 100×21.1 mm) eluting with MeCN/water+0.1% TFA (10% to 100% organic in 10 min, hold 100% in 2 min, 20 mL/min). Related fractions were pooled and evaporated in vacuo to afford an aqueous mixture. The resulting aqueous mixture was extracted with EtOAc, washed with aqueous NaHCO3, dried (Na2SO4), filtered and concentrated to afford a brown glass as the titled compound. LCMS calc.=533.07; found=534.19 (M+H)+.

Workup

  1. customirradiation at 140° C. for 25 min

Sources & evidence

ORD record
ord-0d35a91eb22241fb8fe7f24f4f66eae1
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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