4-Methoxycarbonylphenylboronic acid → HCID 57941487, compound

HRID 1437933Notes

Reaction equation

HRID 1437933 reaction equation
[CH3:1][N:2]1[C:10]2[C@@:9]3([CH3:14])[C:11]([CH3:13])([CH3:12])[C@H:6]([CH2:7][CH2:8]3)[C:5]=2[C:4](=[O:15])[NH:3]1.[CH3:16][O:17][C:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)=[O:19]>ClCCl.N1C=CC=CC=1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:16][O:17][C:18](=[O:19])[C:20]1[CH:25]=[CH:24][C:23]([N:3]2[C:4](=[O:15])[C:5]3[C@@H:6]4[C:11]([CH3:12])([CH3:13])[C@@:9]([CH3:14])([CH2:8][CH2:7]4)[C:10]=3[N:2]2[CH3:1])=[CH:22][CH:21]=1

Participants

6

Reactant 2

HCID 27343694-Methoxycarbonylphenylboronic acidHCID 57941341HCID 57941341, compound2×

Product 1

HCID 57941487HCID 57941487, compoundYield 29.5%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (4S,7R)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 19; 100 mg, 0.48 mmol), 4-methoxycarbonyl-phenyl-boronic acid (180 mg, 0.97 mmol), and copper(II) acetate (133 mg, 0.73 mmol) in dichloromethane (1 mL) and pyridine (0.8 mL) was stirred at room temperature for 2 days. The reaction mixture was evaporated and purified using an Analogix Intelliflash 280 system (Analogix, Inc., Burlington, Wis.) with an Isco 12 g column, eluting with 10-60% ethyl acetate/hexanes to give 4-((4S,7R)-1,7,8,8-tetramethyl-3-oxo-1,3,4,5,6,7-hexahydro-4,7-methano-indazol-2-yl)-benzoic acid methyl ester (48.2 mg, 29%) as an off-white solid. ES(+)-MS (M+H) 341.

Workup

  1. customThe reaction mixture was evaporated
  2. custompurified
  3. washeluting with 10-60% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c80bce213f9b466fb930fcfdb37acde4
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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