Cesium carbonate → Tert-butyl 4-(4-(1-(pyridin-3-yl)azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate

HRID 873560ノート

反応式

HRID 873560 の反応式
[NH:1]1[CH2:4][CH:3]([C:5]([NH:7][C:8]2[CH:27]=[CH:26][C:11]([O:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)=[CH:10][CH:9]=2)=[O:6])[CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>O1CCOCC1.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]>[N:37]1[CH:38]=[CH:39][CH:40]=[C:35]([N:1]2[CH2:4][CH:3]([C:5]([NH:7][C:8]3[CH:9]=[CH:10][C:11]([O:12][CH:13]4[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:17][CH2:18]4)=[CH:26][CH:27]=3)=[O:6])[CH2:2]2)[CH:36]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 122863-BromopyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86702036Tert-butyl 4-(4-(azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate

生成物 1

HCID 86702037Tert-butyl 4-(4-(1-(pyridin-3-yl)azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

tert-Butyl 4-(4-(azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate (4.97 g, 13.24 mmol), cesium carbonate (10.78 g, 33.1 mmol), 3-bromopyridine (1.307 ml, 13.24 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.764 g, 1.32 mmol) and bis(dibenzylideneacetone)palladium(0) (0.606 g, 0.662 mmol) were suspended in dioxane (50 ml), bubbled with nitrogen for 30 minutes and heated at 100° C. overnight. The mixture was filtered through a celite pad with dichloromethane washes and the filtrate was concentrated. Normal phase chromatography provided the title compound.

後処理

  1. custombubbled with nitrogen for 30 minutes
  2. filtrationThe mixture was filtered through a celite pad with dichloromethane washes
  3. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-febb9303495c416daa1e382b7ce2c550
出典データセット
uspto-grants-2015_03
特許番号
US08975398B2

反応ノート

読み込み中…