Hydrochloric Acid → 4-[(Benzylamino)carbonyl]-3-methoxyphenylboronic acid

HRID 897555Notes

Reaction equation

HRID 897555 reaction equation
C([Li])CCC.[CH2:6]([NH:14][C:15](=[O:25])[C:16]1[CH:21]=[CH:20][C:19](Br)=[CH:18][C:17]=1[O:23][CH3:24])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10]C=1.[B:26](OC(C)C)([O:31]C(C)C)[O:27]C(C)C.Cl>O1CCCC1>[CH2:6]([NH:14][C:15]([C:16]1[CH:21]=[CH:20][C:19]([B:26]([OH:31])[OH:27])=[CH:18][C:17]=1[O:23][CH3:24])=[O:25])[C:7]1[CH:8]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 22346935N1-phenethyl-4-bromo-2-methoxybenzamideHCID 178418339Butyllithium

Product 1

HCID 223467454-[(Benzylamino)carbonyl]-3-methoxyphenylboronic acidYield 59.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyl lithium (1.6 M in hexane solution, 8.5 ml, 13.54 mmol) was added slowly to a solution of N1-phenethyl-4-bromo-2-methoxybenzamide (1.81 g, 5.41 mmol) in tetrahydrofuran (40 mL) at −78° C. After 30 minutes, triisopropyl borate (1.87 mL, 8.12 mmol) was added rapidly. The reaction mixture was allowed to warm up to room temperature after 13 minutes and stirred for 3 hours. Hydrochloric acid (2.5N, 40 mL) was added and the mixture was stirred overnight. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash column chromatography using dichloromethane/methanol (95:5) as mobile to give 4-[(benzylamino)carbonyl]-3-methoxyphenylboronic acid (0.916 g, 56%). 1H NMR (DMSO-d6) δ 2.85 (m, 2H), 3.53 (m, 2H) 3.88 (s, 3H), 7.31 (m, 7H), 7.70 (d, J=7.61 Hz, 1H), 8.19 (m, 2H), 9.10 (m, 1H).

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-48e9e5bc85fd4968853963f11859ee12
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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