Hydrochloric Acid → HCID 178485317, compound

HRID 1059211Notes

Reaction equation

HRID 1059211 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][CH3:8])=[O:6].[CH2:12]([Li])CCC.COB(OC)OC.Cl.Br[C:26]1[CH:31]=[CH:30][C:29]([C:32]([C:34]2[N:35]=[CH:36][N:37](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:38]=2)=[O:33])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.CCCCCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:33][CH:32]([C:29]1[CH:28]=[CH:27][C:26]([C:2]2[CH:11]=[CH:10][CH:9]=[C:4]([C:5]([NH:7][CH3:8])=[O:6])[CH:3]=2)=[CH:31][CH:30]=1)[CH2:34][C:38]1[N:37]=[CH:36][NH:35][CH:12]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 10340Sodium CarbonateHCID 42941703-Bromo-N-methylbenzamideHCID 18668547(4-bromophenyl) (1-trityl-1H-imidazol-4-yl)methanoneHCID 178418339Butyllithium

Product 1

HCID 178485317HCID 178485317, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-bromo-N-methylbenzamide (16.0 g) in THF (180 ml) was slowly added dropwise a solution (1.6 M; 103 ml) of n-butyllithium in hexane at −78° C., and the mixture was stirred at −78° C. for 20 min. Trimethoxyborane (50.2 ml) was added dropwise at −78° C. and the mixture was stirred at −78° C. for 30 min and at room temperature for 17 h. 2N Hydrochloric acid (82.0 ml) was added to the reaction mixture, and after stirring for 1 h, the reaction mixture was extracted with ethyl acetate, the organic layer was washed with saturated brine and dried. The solvent was evaporated under reduced pressure to give a crude product (22.5 g) of 3-[(methylamino)carbonyl]phenylboronic acid as a pale-yellow oil. By the reaction in the same manner as in Example 29-(i) using this product (19.2 g), (4-bromophenyl)(1-trityl-1H-imidazol-4-yl)methanone (10.0 g), 2M aqueous sodium carbonate solution (81.2 ml) and tetrakis(triphenylphosphine)palladium(0) (1.17 g), the title compound (6.89 g) was obtained as colorless powder crystals.

Workup

  1. stirringthe mixture was stirred at −78° C. for 30 min and at room temperature for 17 h
  2. stirringafter stirring for 1 h
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. customdried
  6. customThe solvent was evaporated under reduced pressure
  7. customto give a crude product (22.5 g) of 3-[(methylamino)carbonyl]phenylboronic acid as a pale-yellow oil

Sources & evidence

ORD record
ord-fdc603aaace34c92b5be40320e0ae9cf
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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