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Tetrahydrofuran → 8-(4-t-Butyloxycarbonylpiperazin-1-yl)quinoline

HRID 75480
ノート
印刷プレビュー

反応式

HRID 75480 の反応式
[C:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O-:13])=[O:12])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])C.FC(F)(F)S(OC1C=[CH:22][CH:23]=[C:24]2C=1[N:28]=[CH:27][CH:26]=[CH:25]2)(=O)=O.[C:32]([O-])([O-])=O.[Cs+].[Cs+].[CH2:38]1[CH2:42]OC[CH2:39]1>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:3]2[C:24](=[CH:23][CH:22]=[CH:4][C:1]=2[N:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:38]([CH3:39])([CH3:42])[CH3:32])=[O:12])[CH2:9][CH2:10]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 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 36600898-Quinolinyl trifluoromethanesulfonate2 回HCID 226363811-Tert-butyl-4-piperazine carboxylate2 回

生成物 1

HCID 155406788-(4-t-Butyloxycarbonylpiperazin-1-yl)quinoline収率 74%

試薬・触媒・溶媒 3

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

実験手順

t-butyl piperazine-1-carboxylate (compound 31, 8.6 g, 46 mmol) and quinolin-8-yl trifluoromethanesulfonate (compound 30, 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, the residue was purified with normal preparative column to give rise to desired compound (9.3 g, 74% yield) as a 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-aedb96e59e354a708b31212b81df7a88
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08835436B2

反応ノート

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