Neopentyl alcohol → 7-(2-Fluoropyridin-3-yl)-3-(neopentyloxy)-5H-chromeno[2,3-c]pyridin-5-one

HRID 335854

반응식

HRID 335854 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]2[O:8][C:9]3[C:14]([C:15](=[O:16])[C:4]=2[CH:3]=1)=[CH:13][C:12]([C:17]1[C:18]([F:23])=[N:19][CH:20]=[CH:21][CH:22]=1)=[CH:11][CH:10]=3.[CH2:24]([OH:29])[C:25]([CH3:28])([CH3:27])[CH3:26].C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:23][C:18]1[C:17]([C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[O:8][C:5]2[CH:6]=[N:7][C:2]([O:29][CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:3][C:4]=2[C:15]3=[O:16])=[CH:22][CH:21]=[CH:20][N:19]=1

참가 물질

6

반응물 4

HCID 6404Neopentyl alcoholHCID 10796Cesium carbonateHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 866584693-Chloro-7-(2-fluoropyridin-3-yl)-5H-chromeno[2,3-c]pyridin-5-one

생성물 1

HCID 673830307-(2-Fluoropyridin-3-yl)-3-(neopentyloxy)-5H-chromeno[2,3-c]pyridin-5-one수율 18.8%

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

반응 조건

온도
95 °C

실험 절차

A vial was charged with 3-chloro-7-(2-fluoropyridin-3-yl)-5H-chromeno[2,3-c]pyridin-5-one (275 mg, 0.842 mmol), neopentyl alcohol (297 mg, 3.37 mmol), Pd2 dba3 (38.5 mg, 0.042 mmol), racemic-2-(di-t-butylphosphino)-1,1′-binaphthyl (67.1 mg, 0.168 mmol) and cesium carbonate (686 mg, 2.104 mmol). The vial was evacuated and backfilled with nitrogen (procedure was repeated twice). Toluene (1.7 mL) was added, the vial was sealed and the reaction mixture was heated to 95° C. in an oilbath overnight. The reaction mixture was cooled to RT and partitioned between EtOAc and water. The organic phase was separated and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (10-100% EtOAc/hexanes). 7-(2-Fluoropyridin-3-yl)-3-(neopentyloxy)-5H-chromeno[2,3-c]pyridin-5-one (60 mg) was obtained as a yellow powder.

후처리

  1. customThe vial was evacuated
  2. additionToluene (1.7 mL) was added
  3. customthe vial was sealed
  4. temperatureThe reaction mixture was cooled to RT
  5. custompartitioned between EtOAc and water
  6. customThe organic phase was separated
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by flash chromatography (10-100% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-a50f94e6c9ad433fa6044db861798e74
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883782B2

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