Phenylboronic Acid → HCID 23033929、化合物

HRID 1393352ノート

反応式

HRID 1393352 の反応式
C(=O)(O)[O-].[Na+].Br[C:7]1[S:8][C:9]2[C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O.C(COC)OC.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.[Cu]I>[C:19]1([C:7]2[S:8][C:9]3[C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

8

反応物 3

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 230338792-Bromo-1,3-benzothiazole-7-carboxylic acid

生成物 1

HCID 23033929HCID 23033929、化合物収率 78.3%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
50 °C

実験手順

Tetrakis(triphenylphosphine)palladium (144 mg, 0.125 mmol) and a solution of sodium bicarbonate (630 mg, 7.50 mmol) in degassed water (10 ml) were added in turn to a solution of ethyl ester of 2-bromobenzothiazole-7-carboxylic acid (715 mg, 2.50 mmol) and phenyl boronic acid (341 mg, 2.8 mmol) in degassed dimethoxyethane (20 ml) and the mixture was stirred at 50° C. for 10 min. Copper (I) iodide (24 mg, 0.125 mmol) was added to the mixture at room temperature and the mixture was heated under reflux for 4 hrs. Dimethoxyethane was distilled off under reduced pressure and the residue was extracted with ethyl acetate. The organic layer was washed with brine and dried and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=10) to give ethyl ester of 2-phenylbenzothiazole-7-carboxylic acid (500 mg, 70%) as colorless crystals.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. distillationDimethoxyethane was distilled off under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customdried
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=10)

出典と根拠

ORDレコード
ord-74687d80904c4c35b0ab8edea982053f
出典データセット
uspto-grants-2008_03
特許番号
US07345068B2

反応ノート

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