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

HRID 2088403

반응식

HRID 2088403 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-358414a1b6004d7abe093fc8b5d47d65
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08435986B2

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