반응 #171685

ord-e68af114d83347c78e7a8d2195b9a385

반응 방정식

CN(C(=O)c1cc2c(s1)-c1ccc(Br)cc1OCC2)c1ccccc1Cl
8-bromo-N-(2-chlorophenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide
COC(=O)Cc1cccc(B2OC(C)(C)C(C)(C)O2)c1
methyl 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate
CC(=O)[O-].[K+]
potassium acetate
→
COC(=O)Cc1cccc(-c2ccc3c(c2)OCCc2cc(C(=O)N(C)c4ccccc4Cl)sc2-3)c1
200
COC(=O)Cc1cccc(-c2ccc3c(c2)OCCc2cc(C(=O)N(C)c4ccccc4Cl)sc2-3)c1
methyl 2-(3-(2-((2-chlorophenyl)(methyl)carbamoyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-8-yl)phenyl)acetate

반응물

CN(C(=O)c1cc2c(s1)-c1ccc(Br)cc1OCC2)c1ccccc1Cl
8-bromo-N-(2-chlorophenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide
COC(=O)Cc1cccc(B2OC(C)(C)C(C)(C)O2)c1
methyl 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate
CC(=O)[O-].[K+]
potassium acetate

시약

[Cl][Pd][Cl].[Fe+2].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1
Pd(dppf)Cl2

용매

CC#N
acetonitrile
CS(C)=O
DMSO

반응 조건

온도
80°CELSIUS
상세 조건
See reaction.notes.procedure_details.

실험 절차

Following the procedure of Example 93, 8-bromo-N-(2-chlorophenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide 150, methyl 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate, potassium acetate, and Pd(dppf)Cl2 in acetonitrile and DMSO were heated at 80° C. overnight to give 200. MS: (ESI+) 518.2

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08846762B2uspto-grants-2014_09