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

HRID 897552
Notes
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Reaction equation

HRID 897552 reaction equation
C([Li])CCC.[CH2:6]([NH:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][C:18](Br)=[CH:17][C:16]=1[O:22][CH3:23])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[B:25](OC(C)C)([O:30]C(C)C)[O:26]C(C)C.Cl>O1CCCC1>[CH2:6]([NH:13][C:14]([C:15]1[CH:20]=[CH:19][C:18]([B:25]([OH:30])[OH:26])=[CH:17][C:16]=1[O:22][CH3:23])=[O:24])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 22346886N-benzyl-4-bromo-2-methoxybenzamideHCID 178418339Butyllithium

Product 1

HCID 223467454-[(Benzylamino)carbonyl]-3-methoxyphenylboronic acidYield 46%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

n-Butyl lithium(1.6 M in hexane solution, 8.0 ml, 12.88 mmol) was added slowly to a solution of N1-benzyl-4-bromo-2-methoxybenzamide (1.65 g, 5.15 mmol) in tetrahydrofuran (40 mL) at −78° C. After 30 minutes, triisopropyl borate (1.8 mL, 7.73 mmol) was added rapidly. The reaction mixture was allowed to warm up to room temperature after 13 minutes and stirred for 16 hours. Hydrochloric acid (2.5N, 36 mL) was added and the mixture was stirred overnight. Organic solvent was removed 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 phase to give 4-[(benzylamino)carbonyl]-3-methoxyphenylboronic acid (0.675 g, 46%). 1H NMR (DMSO-d6) δ 3.90 (s, 3H), 4.51 (d, J=6.18 Hz, 2H), 7.24 (m, 1H), 7.34 (m, 4H), 7.43 (d, J=7.55 Hz, 1H), 7.59 (s, 1H), 7.69 (d, J=7.55 Hz, 1H), 8.23 (s, 2H), 8.69 (m, 1H).

Workup

  1. stirringthe mixture was stirred overnight
  2. customOrganic solvent was removed
  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-e633509107e14778a958e7489a0f654e
Source dataset
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06921763B2

Reaction notes

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