Dichloromethane → HCID 66658923, compound

HRID 420825Notes

Reaction equation

HRID 420825 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]([CH3:24])[CH2:16][NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[CH:11][CH:10]=2)O1.[C:26]([C:28]1[CH:29]=[C:30]([CH:36]=[CH:37][C:38]=1OS(C(F)(F)F)(=O)=O)[C:31]([O:33][CH2:34][CH3:35])=[O:32])#[N:27].C(Cl)Cl.CC([O-])=O.[K+]>COCCOC.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].O.CCO>[C:26]([C:28]1[CH:29]=[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:36]=[CH:37][C:38]=1[C:9]1[CH:10]=[CH:11][C:12]([C@H:15]([CH3:24])[CH2:16][NH:17][S:18]([CH:21]([CH3:22])[CH3:23])(=[O:19])=[O:20])=[CH:13][CH:14]=1)#[N:27]

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 59120696HCID 59120696, compoundHCID 87093775HCID 87093775, compound

Product 1

HCID 66658923HCID 66658923, compoundYield 74%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Stir a solution of (2R)-propane-2-sulfonic acid {2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-amide (50 g, 136.2 mmol), Ethyl 3-Cyano-4-trifluoromethanesulfonyloxy-benzoate (40 g, 123.8 mmol), PdCl2(dppf).DCM (3.03 g, 3.71 mmol) and KOAc (36.43 g, 371.4 mmol) in DME:EtOH:H2O (200 mL/200 mL/200 mL) under nitrogen at 80° C. for 50 minutes. Pour the reaction mixture into ice-water and extract it with EtOAc. Wash the organic layer with water and saturated aq. sodium chloride solution, dry over MgSO4, filter and concentrate it in vacuo. Subject residue to silica gel chromatography eluting with hexane/EtOAc 4:1 to 3:1. Triturate the product in hexane, filter and dry, to yield 37.95 g of 1-(S)-Ethyl 2-Cyano-4′-[1-methyl-2-(propane-2-sulfonylamino)-ethyl]-biphenyl-4-carboxylate (74%). MS(ES): m/z=413.1 [M-H].

Workup

  1. extractionextract it with EtOAc
  2. washWash the organic layer with water and saturated aq. sodium chloride solution
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate it in vacuo
  6. washSubject residue to silica gel chromatography eluting with hexane/EtOAc 4:1 to 3:1
  7. customTriturate the product in hexane
  8. filtrationfilter
  9. customdry

Sources & evidence

ORD record
ord-dce90cacff3f4f2a981c1fc36d66642b
Source dataset
uspto-grants-2012_01
Patent number
US08097652B2

Reaction notes

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