Hydrochloric Acid → HCID 178485317、化合物

HRID 1059211ノート

反応式

HRID 1059211 の反応式
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

参加物

10

反応物 6

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

生成物 1

HCID 178485317HCID 178485317、化合物

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fdc603aaace34c92b5be40320e0ae9cf
出典データセット
uspto-grants-2003_02
特許番号
US06518257B1

反応ノート

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