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Cesium carbonate → 8-(4-t-Butyloxycarbonylpiperazin-1-yl)quinoline

HRID 339734
ノート
印刷プレビュー

反応式

HRID 339734 の反応式
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.FC(F)(F)S(O[C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[N:28]=[CH:27][CH:26]=[CH:25]2)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[N:28]1[C:29]2[C:24](=[CH:23][CH:22]=[CH:21][C:20]=2[N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[CH:25]=[CH:26][CH:27]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 36600898-Quinolinyl trifluoromethanesulfonate

生成物 1

HCID 155406788-(4-t-Butyloxycarbonylpiperazin-1-yl)quinoline収率 74.9%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒
HCID 634876
Binap, (A+-)-
触媒
HCID 3283Diethyl Ether溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

t-Butyl piperazine-1-carboxylate (8.6 g, 46 mmol) and quinolin-8-yl trifluoromethanesulfonate (11 g, 39.6 mmol) were added to a solution of Cs2CO3 (18 g, 55 mmol), BINAP (1.07 g) and Pd(OAc)2 (367 mg) in THF (100 ml). The reaction mixture was refluxed for 1 day and then cooled down to room temperature. The resulting solution was diluted with Et2O (100 ml) and then filtered with Celite. The organic solution was evaporated under reduced pressure, and the residue was purified with normal preparative column to give rise to desired compound (9.3 g, 74% yield) as light yellow solid.

後処理

  1. temperatureThe reaction mixture was refluxed for 1 day
  2. filtrationfiltered with Celite
  3. customThe organic solution was evaporated under reduced pressure
  4. customthe residue was purified with normal preparative column

出典と根拠

ORDレコード
ord-b5efeb08621741949fdae58834bc93a9
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08895558B2

反応ノート

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