Cesium fluoride → [4-(2-Azepan-1-yl-ethoxy)-phenyl]-[6-methoxy-2-(2,3,5-trifluorophenyl)-naphthalen-1-yl]-methanone

HRID 1513968노트

반응식

HRID 1513968 반응식
[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:38]=[CH:37][C:14]([C:15]([C:17]3[C:26]4[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=4)[CH:20]=[CH:19][C:18]=3OS(C(F)(F)F)(=O)=O)=[O:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F-].[Cs+].Br[C:42]1[CH:47]=[C:46]([F:48])[CH:45]=[C:44]([F:49])[C:43]=1[F:50]>C(#N)C.[Pd].C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.[Pd]>[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([C:17]3[C:26]4[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=4)[CH:20]=[CH:19][C:18]=3[C:42]3[CH:47]=[C:46]([F:48])[CH:45]=[C:44]([F:49])[C:43]=3[F:50])=[O:16])=[CH:37][CH:38]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

참가 물질

7

반응물 3

HCID 25953Cesium fluorideHCID 27363991-Bromo-2,3,5-trifluorobenzeneHCID 57552509Trifluoromethanesulfonic acid 1-[4-(2-azepan-1-yl-ethoxy)-benzoyl]-6-methoxynaphthalen-2-yl ester

생성물 1

HCID 57552540[4-(2-Azepan-1-yl-ethoxy)-phenyl]-[6-methoxy-2-(2,3,5-trifluorophenyl)-naphthalen-1-yl]-methanone

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 2734559Bis(tricyclohexylphosphine) palladium(0)촉매HCID 6342Acetonitrile용매

실험 절차

Dissolve trifluoromethanesulfonic acid 1-[4-(2-azepan-1-yl-ethoxy)-benzoyl]-6-methoxynaphthalen-2-yl ester (2.60 g, 6.53 mmol) in 200 mL acetonitrile and add to this bis(pinacoloato)diboron (1.5 g, 7.96 mmol), bis(tricyclohexylphosphine)palladium (0) (0.72 g, 1.50 mmol) and cesium fluoride (7.33 g, 67.0 mmol). Heat the reaction to 100° C. until LC/MS indicates all starting material is consumed. Add to this mixture 1-bromo-2,3,5-trifluorobenzene (2.00 g, 13.06 mmol) and another 720 mg of palladium catalyst and heat at 80° C. for 24 hours. Filter the reaction, concentrate filtrate and purify on a silica gel column eluting with a 0-10% methanol/methylene chloride gradient. The yield is 1.85 g (53%)

후처리

  1. temperatureHeat
  2. customthe reaction to 100° C. until LC/MS
  3. customis consumed
  4. filtrationFilter
  5. customthe reaction
  6. concentrationconcentrate filtrate
  7. custompurify on a silica gel column
  8. washeluting with a 0-10% methanol/methylene chloride gradient

출처 및 근거

ORD 기록
ord-99f37703d60e4d299ea6b20b3488e082
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217032B2

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