Sodium Carbonate → 1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-4-yl)phenoxy)propan-2-ol

HRID 1399890ノート

反応式

HRID 1399890 の反応式
Br[C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][N:20]1[CH2:29][CH:30]([OH:48])[CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:34]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][N:20]1[CH2:29][CH:30]([OH:48])[CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:2]2[C:10]3[N:9]=[CH:8][N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH:34]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 867292361-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)propan-2-olHCID 86729285HCID 86729285、化合物

生成物 1

HCID 867292841-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-4-yl)phenoxy)propan-2-ol収率 82%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole (200 mg, 0.611 mmol), 1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)propan-2-ol (375 mg, 0.916 mmol), Pd(dppf)Cl2 (89 mg, 0.12 mmol) and Na2CO3 (130 mg, 1.22 mmol) in dioxane and H2O was stirred under N2 atmosphere at 100° C. for 3 h. The mixture was extracted with DCM and the combined organic layers dried over Na2SO4 and concentrated in vacuum to give the crude product (265 mg, Yield 82%) which was used without further purification.

後処理

  1. extractionThe mixture was extracted with DCM
  2. dry with materialthe combined organic layers dried over Na2SO4
  3. concentrationconcentrated in vacuum

出典と根拠

ORDレコード
ord-cf1550b8bb2742659a48d245f3f3b856
出典データセット
uspto-grants-2014_12
特許番号
US08906900B2

反応ノート

読み込み中…