2-Methyl-4-methoxycarbonylphenylboronic acid, pinacol ester → HCID 69652532, compound

HRID 1794017Notes

Reaction equation

HRID 1794017 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7](B2OC(C)(C)C(C)(C)O2)=[C:6]([CH3:19])[CH:5]=1.FC(F)(F)S(O[C:27]1[CH2:32][CH2:31][CH2:30][CH2:29][C:28]=1[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=1)(=O)=O>>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:27]2[CH2:32][CH2:31][CH2:30][CH2:29][C:28]=2[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=2)=[C:6]([CH3:19])[CH:5]=1

Participants

3

Reactant 2

HCID 110870242-Methyl-4-methoxycarbonylphenylboronic acid, pinacol esterHCID 22219700HCID 22219700, compound

Product 1

HCID 69652532HCID 69652532, compoundYield 53.4%

Procedure

3-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester of Example 28, Step A (0.300 g, 1.09 mmol) and 2-(3-methoxy-phenyl)-cyclohex-1-en-1-yl trifluoromethanesulfonate (0.441 g, 1.31 mmol) were reacted in the manner of Example 1, Step F. Purification by flash column chromatography on silica gel, eluting with a solvent gradient of from 0 to 5% ethyl acetate in hexane, afforded the title compound (0.196 g) as a light yellow oil.

Workup

  1. customPurification by flash column chromatography on silica gel
  2. washeluting with a solvent gradient of from 0 to 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8a0a4fa1cb794deaa9e39dbc55d67f97
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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