Sodium Carbonate → HCID 178455346, compound

HRID 2235306Notes

Reaction equation

HRID 2235306 reaction equation
Br[C:2]1[CH:29]=[CH:28][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][CH2:10][N:9]([C@H:13]3[CH2:18][CH2:17][C@H:16]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:15][CH2:14]3)[C:8]2=[O:27])=[C:4]([Cl:30])[CH:3]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33](B(O)O)[CH:32]=1.C([O-])([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>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.COCCOC.O>[C:23]([Si:20]([CH3:21])([CH3:22])[O:19][C@H:16]1[CH2:17][CH2:18][C@H:13]([N:9]2[CH2:10][CH2:11][CH2:12][CH:7]([CH2:6][C:5]3[CH:28]=[CH:29][C:2]([C:33]4[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=4)=[CH:3][C:4]=3[Cl:30])[C:8]2=[O:27])[CH2:14][CH2:15]1)([CH3:24])([CH3:26])[CH3:25]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 27343783-Pyridinylboronic acidHCID 178455345HCID 178455345, compound

Product 1

HCID 178455346HCID 178455346, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Combine trans-3-(4 bromo-2-chloro-benzyl)-1-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-piperidin-2-one (Preparation 65) (0.2 g, 0.49 mmol), 3-pyridine boronic acid (0.2 g, 1.49 mmol), tetrakis(triphenylphosphine)palladium(0) (0.06 g, 0.05 mmol), Na2CO3 (1.1 g, 9.95 mmols), water (1.5 mL), 1,2-dimethoxy-ethane (7 mL) and heat at 80° C. for 24 hours. Cool the reaction mixture to room temperature, add saturated aqueous NaHCO3 (5 mL) and extract with EtOAc (3×10 mL). Dry the organic.layer over anhydrous Na2SO4, remove the solvent and purify the residue by chromatography over silica gel (eluting with 50 to 100% EtOAc in hexane) to obtain trans-1-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-3-(2-chloro-4-pyridine-3-yl-benzyl)-piperidin-2-one as a white solid (0.2 g, 80%).

Workup

  1. extractionextract with EtOAc (3×10 mL)
  2. dry with materialDry the organic.layer over anhydrous Na2SO4
  3. customremove the solvent
  4. custompurify the residue by chromatography over silica gel (eluting with 50 to 100% EtOAc in hexane)

Sources & evidence

ORD record
ord-ef248663f1354ad3b59d863b63a7a19a
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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