Potassium Phosphate, Tribasic → (3-(5-Methylpyridin-2-yl)phenyl)methanol

HRID 2088403

反応式

HRID 2088403 の反応式
P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=1.[OH:17][CH2:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1>O1CCOCC1.O.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>[CH3:16][C:13]1[CH:14]=[CH:15][C:10]([C:23]2[CH:24]=[C:19]([CH2:18][OH:17])[CH:20]=[CH:21][CH:22]=2)=[N:11][CH:12]=1

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 5642162-Bromo-5-methylpyridineHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acid

生成物 1

HCID 56604357(3-(5-Methylpyridin-2-yl)phenyl)methanol

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

92 mg (0.08 mmol) of tetrakis(triphenylphosphine)palladium are added to a suspension, kept under nitrogen, of 849 mg (4.0 mmol) of tripotassium phosphate, 344 mg (2.0 mmol) of 2-bromo-5-methylpyridine and 304 mg (2.0 mmol) of 3-hydroxymethylbenzeneboronic acid in 12 ml of dioxane and 1 ml of water, and the mixture is heated at the boil with stirring for 18 hours. The reaction mixture is cooled to room temperature and partitioned between water and ethyl acetate. The organic phase is dried over sodium sulfate, evaporated, and the residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent: [3-(5-methylpyridin-2-yl)phenyl]methanol as yellowish oil; LCMS 200.

後処理

  1. temperaturethe mixture is heated at the boil
  2. custompartitioned between water and ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated
  5. customthe residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent

出典と根拠

ORDレコード
ord-358414a1b6004d7abe093fc8b5d47d65
出典データセット
uspto-grants-2013_05
特許番号
US08435986B2

関連ノート

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