反応 #360813

ord-68a7a76c99d74027bf1b56a06e811d6c

反応方程式

CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(C#N)cc4)o3)cc2)CC1
p-CN Core
BrCc1ccc(-c2ccccc2)cc1
4PhPh
→
N#Cc1ccc(-c2ccc(C(=O)N(Cc3ccc(-c4ccccc4)cc3)c3ccc(N4CCNCC4)cc3)o2)cc1
MK2_Alk_22
収率 50.0%
CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(C#N)cc4)o3)cc2)CC1
p-CN Core
CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(C#N)cc4)o3)cc2)CC1
MK2_Core_CN

反応物

CC(C)(C)OC(=O)N1CCN(c2ccc(NC(=O)c3ccc(-c4ccc(C#N)cc4)o3)cc2)CC1
p-CN Core
BrCc1ccc(-c2ccccc2)cc1
4PhPh

試薬

O=S(=O)(O)O
H2SO4
[Li][N]([Si](C)(C)C)[Si](C)(C)C
LiHMDS

溶媒

COCCOCCOC
diglyme
CN(C)C=O
DMF
CN(C)C=O
DMF
CN(C)C=O
DMF

反応条件

温度
23°CELSIUS

後処理

  1. 1
    workup.ADDITIONquenched by addition of saturated aqueous NaHCO3 (2 uL) and diluted with water (1 uL) and DMSO (2 uL)
  2. 2
    workup.ADDITIONquenched by addition of saturated aqueous NaHCO3 (2 uL) and diluted with water (1 uL) and DMSO (2 uL)
  3. 3
    workup.ADDITIONquenched by addition of saturated aqueous NaHCO3 (2 uL) and diluted with water (1 uL) and DMSO (2 uL)
  4. 4
    workup.ADDITIONThe reactions were further diluted to 10 mM using DMSO.

出典

DOI: 10.1038/s44160-023-00351-1Cernak miniaturized N-alkylation with BOC deprotection