Phenylboronic Acid → (4-Methoxyphenyl)boronic acid

HRID 500342Notes

Reaction equation

HRID 500342 reaction equation
C(OC(N1CC(OC2[C:23]3[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=3)C=CN=2)CC1C(O)=O)=O)(C)(C)C.C1([B:35]([OH:37])[OH:36])C=CC=CC=1.CC(C)([O-])C.[Na+]>C1COCC1>[CH3:25][O:24][C:20]1[CH:21]=[CH:22][C:23]([B:35]([OH:37])[OH:36])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 66827Phenylboronic AcidHCID 23595300HCID 23595300, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 201262(4-Methoxyphenyl)boronic acidYield 236.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(6-methoxy-isoquinolin-1-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (39 mg, 0.10 mmol), phenylboronic acid (14.6 mg, 0.12 mmol), sodium tert-butoxide (38 mg, 0.40 mmol) and ((t-Bu)2POH)2PdCl2 (POPd) (5 mg, 0.01 mmol) in THF (2 mL) was heated to reflux for 4 h. After cooling down, the formed mixture was quenched with 5% citric acid (aq) and extracted with EtOAc (20 mL). The organic layer was washed with brine, dried over MgSO4, filtered, evaporated. The residue was purified by prep-HPLC to yield 36 mg (83%) of the desired product as an off-white foam.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. temperatureAfter cooling down
  4. customthe formed mixture was quenched with 5% citric acid (aq)
  5. extractionextracted with EtOAc (20 mL)
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-4ee3a306ec5147cba736cd285e65b016
Source dataset
uspto-grants-2010_08
Patent number
US07772180B2

Reaction notes

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