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

HRID 1513968ノート

反応式

HRID 1513968 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 2734559Bis(tricyclohexylphosphine) palladium(0)触媒HCID 6342Acetonitrile溶媒

実験手順

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%)

後処理

  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

出典と根拠

ORDレコード
ord-99f37703d60e4d299ea6b20b3488e082
出典データセット
uspto-grants-2012_07
特許番号
US08217032B2

反応ノート

読み込み中…