Dichloromethane → HCID 66771970, compound

HRID 1697708Notes

Reaction equation

HRID 1697708 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([C@H:11]2[CH2:15][N:14]([C:16]3[N:20]([CH:21]4[CH2:24][CH2:23][CH2:22]4)[N:19]=[C:18]([CH3:25])[CH:17]=3)[C@H:13]([C:26]([NH:28][C:29]3([C:32]#[N:33])[CH2:31][CH2:30]3)=[O:27])[CH2:12]2)(=[O:10])=[O:9])=[C:4]([C:34]([F:37])([F:36])[F:35])[CH:3]=1.CC1(C)C(C)(C)[O:42][B:41](B2OC(C)(C)C(C)(C)O2)[O:40]1.ClCCl.C([O-])(=O)C.[K+]>CS(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:32]([C:29]1([NH:28][C:26]([C@H:13]2[N:14]([C:16]3[N:20]([CH:21]4[CH2:24][CH2:23][CH2:22]4)[N:19]=[C:18]([CH3:25])[CH:17]=3)[CH2:15][C@H:11]([S:8]([C:5]3[CH:6]=[CH:7][C:2]([B:41]([OH:42])[OH:40])=[CH:3][C:4]=3[C:34]([F:37])([F:36])[F:35])(=[O:10])=[O:9])[CH2:12]2)=[O:27])[CH2:31][CH2:30]1)#[N:33]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 66771969HCID 66771969, compound

Product 1

HCID 66771970HCID 66771970, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of (2S,4R)-4-(4-bromo-2-(trifluoromethyl)phenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-cyclobutyl-3-methyl-1H-pyrazol-5-yl)pyrrolidine-2-carboxamide (40 mg, 66.6 umol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (33.8 mg, 133 umol; CAS Reg. No. 73183-34-3), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride 1:1 complex with dichloromethane (10.9 mg, 13.3 umol) and potassium acetate (32.7 mg, 333 umol) in DMSO (0.8 ml) was heated to 80° C. for 20 h. The reaction mixture was cooled to ambient temperature and poured onto 20 ml 0.1 N HCl/ice/brine and extracted with iPrOAc (2×25 ml). The combined organic layers were washed with 0.1 N HCl/ice/brine (3×), icewater/brine (3×), dried over sodium sulfate and filtered. The solvent was evaporated under reduced pressure to give the crude title compound (66 mg; quant.) which was used in the next reaction step without further purification. MS (ESI): m/z=566.2 [M+H]+.

Workup

  1. extractionextracted with iPrOAc (2×25 ml)
  2. washThe combined organic layers were washed with 0.1 N HCl/ice/brine (3×)
  3. dry with materialicewater/brine (3×), dried over sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9ee448026fe843fdb7a352f26849b22f
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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