Cesium carbonate → Tert-butyl 4-(2-(7-(2-methoxyethoxy)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperazine-1-carboxylate

HRID 1041953ノート

反応式

HRID 1041953 の反応式
FC(F)(F)S(O[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([C:17]1[N:21]3[CH:22]=[CH:23][C:24]([O:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:25][C:20]3=[N:19][N:18]=1)[CH:13]=[CH:12]2)(=O)=O.[N:33]1([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:30][O:29][CH2:28][CH2:27][O:26][C:24]1[CH:23]=[CH:22][N:21]2[C:17]([C:14]3[CH:13]=[CH:12][C:11]4[C:16](=[C:7]([N:36]5[CH2:35][CH2:34][N:33]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:38][CH2:37]5)[CH:8]=[CH:9][CH:10]=4)[N:15]=3)=[N:18][N:19]=[C:20]2[CH:25]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 866543412-(7-(2-Methoxyethoxy)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl trifluoromethane sulfonate

生成物 1

HCID 67234014Tert-butyl 4-(2-(7-(2-methoxyethoxy)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperazine-1-carboxylate収率 76%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

2-(7-(2-methoxyethoxy)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl trifluoromethane sulfonate (0.027 g, 0.0576 mmol), tert-butyl piperazine-1-carboxylate (0.0215 g, 0.115 mmol), Cs2CO3 (0.0282 g, 0.0865 mmol), Pd2 dba3 (0.00528 g, 0.00576 mmol) and Binap-rac (0.00718 g, 0.0115 mmol) were combined in toluene (0.5 mL) in a sealed vial. The reaction mixture was stirred at 100° C. for 16 hours then concentrated under reduced pressure. The resulting residue was diluted with EtOAc, washed with aqueous saturated NaHCO3 and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to an orange solid. Purification via flash column chromatography (40:1 DCM/MeOH followed by 20:1 DCM/MeOH) provided 22 mg (76%) of desired product.

後処理

  1. concentrationthen concentrated under reduced pressure
  2. additionThe resulting residue was diluted with EtOAc
  3. washwashed with aqueous saturated NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to an orange solid
  7. customPurification via flash column chromatography (40:1 DCM/MeOH followed by 20:1 DCM/MeOH)

出典と根拠

ORDレコード
ord-1bdead5f846643718f3b00be4ce1a634
出典データセット
uspto-grants-2013_10
特許番号
US08557809B2

反応ノート

読み込み中…