Ethyl Acetate → HCID 178480068, compound

HRID 1013837Notes

Reaction equation

HRID 1013837 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[C:6]([Cl:31])[C:7]=1[CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:22][CH2:21][C:20]3[C:16](=[CH:17][N:18](S(C(F)(F)F)(=O)=O)[N:19]=3)[CH2:15]2)[C:10]1=[O:30].[CH3:40][N:41]1[CH:45]=[C:44](B2OC(C)(C)C(C)(C)O2)[CH:43]=[N:42]1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:44]2[CH:43]=[N:42][N:41]([CH3:40])[CH:45]=2)[CH:5]=[C:6]([Cl:31])[C:7]=1[CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:22][CH2:21][C:20]3[C:16](=[CH:17][NH:18][N:19]=3)[CH2:15]2)[C:10]1=[O:30]

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 57671341Trifluoro-methanesulfonic acid 3,5-dichloro-4-[2-oxo-1-(2-trifluoromethanesulfonyl-4,5,6,7-tetrahydro-2H-indazol-5-yl)-pyrrolidin-3-ylmethyl]-phenyl ester

Product 1

HCID 178480068HCID 178480068, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Combine trifluoro-methanesulfonic acid 3,5-dichloro-4-[2-oxo-1-(2-trifluoromethanesulfonyl-4,5,6,7-tetrahydro-2H-indazol-5-yl)-pyrrolidin-3-ylmethyl]phenyl ester (Preparation 33) (0.5, 0.77 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.484 g, 2.3 mmol), sodium carbonate (2.7 ml of 2.0 M, 5.4 mmol) in DME (12 mL) and degas with a stream of nitrogen. Add (Ph3P)4Pd (0.089 g, 0.07 mmol), and stir at 80° C. for 4 hour under nitrogen atmosphere. Cool to ambient temperature and add ethyl acetate (20 mL) and water (10 mL). Extract the aqueous phase with ethyl acetate (2×20 mL), dry (sodium sulfate) and condense under reduced pressure. Chromatography (silica, 95:5 CH2Cl2/MeOH) yields 0.144 g (42%) as a white solid MS (m/z): 445 (M+1).

Workup

  1. extractionExtract the aqueous phase with ethyl acetate (2×20 mL)
  2. customdry
  3. custom(sodium sulfate) and condense under reduced pressure

Sources & evidence

ORD record
ord-09dd9da016f4465883d6356104e92030
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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