Sodium Carbonate → HCID 178515668, compound

HRID 1672741Notes

Reaction equation

HRID 1672741 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[C:6]([Cl:22])[C:7]=1[CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([F:20])[CH2:16][CH2:15]2)[C:10]1=[O:21].[N:31]1[CH:36]=[CH:35][CH:34]=[C:33](B(O)O)[CH:32]=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.C([O-])(O)=O.[Na+].CCOC(C)=O.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>[Cl:1][C:2]1[CH:3]=[C:4]([C:33]2[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=2)[CH:5]=[C:6]([Cl:22])[C:7]=1[CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([F:20])[CH2:16][CH2:15]2)[C:10]1=[O:21]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 178515678HCID 178515678, compound

Product 1

HCID 178515668HCID 178515668, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Heat a solution of trifluoro-methanesulfonic acid 3,5-dichloro-4-[trans-1-(4-fluoro-cyclohexyl)-2-oxo-pyrrolidin-3-ylmethyl]-phenyl ester (Preparation 28) (0.346 g, 0.705 mmol), pyridine-3-boronic acid (0.173 g, 1.41 mmol), Pd(PPh3)4 (81 mg), 7 mL of 0.1 M Na2CO3 aq solution in 7 mL of dimethoxy ethane at 80° C. for 24 h. Cool the mixture to room temp and dilute with 20 mL of 1N NaHCO3. Dilute the mixture with 20 mL of EtOAc. Wash the organic layer with water, brine and dry over Na2SO4, filter and concentrate. Purify the crude material by chromatography to afford the title compound: mass spectrum (m/z): 421 (M+1).

Workup

  1. washWash the organic layer with water, brine
  2. dry with materialdry over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the crude material by chromatography

Sources & evidence

ORD record
ord-f0705aeeb22749a8854da2214040323a
Source dataset
uspto-grants-2011_08
Patent number
US07998999B2

Reaction notes

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