Cesium carbonate → tert-butyl 4-(1-(3-(methylthio)-1-phenyl-1H-indazol-6-yl)azetidin-3-yl)piperazine-1-carboxylate

HRID 68684ノート

反応式

HRID 68684 の反応式
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([S:17][CH3:18])=[N:7][N:8]2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[NH:19]1[CH2:22][CH:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)[CH2:20]1.C([O-])([O-])=O.[Cs+].[Cs+].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>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:18][S:17][C:6]1[C:5]2[C:9](=[CH:10][C:2]([N:19]3[CH2:22][CH:21]([N:23]4[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]4)[CH2:20]3)=[CH:3][CH:4]=2)[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 21183794tert-Butyl 4-(azetidin-3-yl)piperazine-1-carboxylateHCID 67448855HCID 67448855、化合物

生成物 1

HCID 67449337tert-butyl 4-(1-(3-(methylthio)-1-phenyl-1H-indazol-6-yl)azetidin-3-yl)piperazine-1-carboxylate

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

実験手順

Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 6-bromo-3-(methylthio)-1-phenyl-1H-indazole (300 mg, 0.94 mmol, 1.00 equiv) in toluene (20 mL), tert-butyl 4-(azetidin-3-yl)piperazine-1-carboxylate (270 mg, 1.12 mmol, 1.20 equiv), Cs2CO3 (430 mg, 1.32 mmol, 1.40 equiv), Pd(OAc)2 (a catalytic amount), BINAP (a catalytic amount). The resulting solution was heated to reflux overnight in an oil bath. The solids were filtered out. The filtrate was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1) to yield tert-butyl 4-(1-(3-(methylthio)-1-phenyl-1H-indazol-6-yl)azetidin-3-yl)piperazine-1-carboxylate as a yellow solid. MS: 480 (MH+).

後処理

  1. customInto a 50-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux overnight in an oil bath
  5. filtrationThe solids were filtered out
  6. concentrationThe filtrate was concentrated under vacuum

出典と根拠

ORDレコード
ord-0beb763fc720402ba1190a2035352297
出典データセット
uspto-grants-2014_09
特許番号
US08822447B2

反応ノート

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