2-Cyclohexen-1-one → 3-(2-Fluoropyridin-3-yl)cyclohex-2-enone

HRID 473656

反応式

HRID 473656 の反応式
Br[C:2]1[C:3]([F:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:9]1(=[O:15])[CH2:14][CH2:13][CH2:12][CH:11]=[CH:10]1.C1(CNCC2CCCCC2)CCCCC1>O1CCOCC1.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>[F:8][C:3]1[C:2]([C:11]2[CH2:12][CH2:13][CH2:14][C:9](=[O:15])[CH:10]=2)=[CH:7][CH:6]=[CH:5][N:4]=1

参加物

6

反応物 3

HCID 135942-Cyclohexen-1-oneHCID 27627783-Bromo-2-fluoropyridineHCID 4594378Bis(cyclohexylmethyl)amine

生成物 1

HCID 593269873-(2-Fluoropyridin-3-yl)cyclohex-2-enone

試薬・触媒・溶媒 2

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

実験手順

A solution of 3-bromo-2-fluoropyridine (11 g, 62.5 mmol), 2-cyclohexen-1-one (24.03 g, 250 mmol), N,N-dicyclohexylmethylamine (30.5 g, 156 mmol) and bis(tri-t-butylphosphine)palladium (0) (0.958 g, 1.875 mmol) in dioxane (80 mL) was heated to 105° C. for 6 h. The mixture was cooled to RT and the dioxane was evaporated under reduced pressure. Water (200 ml) was added and the mixture layer was extracted with EtOAc (2×200 ml). The combined organic layers were washed with brine and dried over sodium sulfate. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (20% to 50% EtOAc in hexanes) afforded 3-(2-fluoropyridin-3-yl)cyclohex-2-enone as colorless crystals. MS (ESI, pos. ion) m/z: 191.9 (M+1).

後処理

  1. customthe dioxane was evaporated under reduced pressure
  2. additionWater (200 ml) was added
  3. extractionthe mixture layer was extracted with EtOAc (2×200 ml)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltration and concentration under reduced pressure

出典と根拠

ORDレコード
ord-3e9a7e1795a3493ea99928bf3e76f863
出典データセット
uspto-grants-2014_01
特許番号
US08637500B2

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