تفاعل #162144

ord-63f9388e3d49420ca475eac23a69f6c9

معادلة التفاعل

Cc1ccc(S(=O)(=O)n2cc(B3OC(C)(C)C(C)(C)O3)c3cc(Cl)cnc32)cc1
LiOH
Cc1ccc(S(=O)(=O)n2cc(B3OC(C)(C)C(C)(C)O3)c3cc(Cl)cnc32)cc1
5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine
Cc1ccc(S(=O)(=O)n2cc(-c3ncc(F)c(S(C)=O)n3)c3cc(Cl)cnc32)cc1
EDCI
Cc1ccc(S(=O)(=O)n2cc(-c3ncc(F)c(S(C)=O)n3)c3cc(Cl)cnc32)cc1
5-chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine
On1nnc2cccnc21
HOAt
CCN(C(C)C)C(C)C
iPr2NEt
CN1CCC(N)C1=O
3-amino-1-methylpyrrolidin-2-one
→
CC1(C)CCCCC(=O)N1Nc1nc(-c2c[nH]c3ncc(Cl)cc23)ncc1F
(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-7,7-dimethylazepan-2-one

المتفاعلات

Cc1ccc(S(=O)(=O)n2cc(B3OC(C)(C)C(C)(C)O3)c3cc(Cl)cnc32)cc1
LiOH
Cc1ccc(S(=O)(=O)n2cc(B3OC(C)(C)C(C)(C)O3)c3cc(Cl)cnc32)cc1
5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine
Cc1ccc(S(=O)(=O)n2cc(-c3ncc(F)c(S(C)=O)n3)c3cc(Cl)cnc32)cc1
EDCI
Cc1ccc(S(=O)(=O)n2cc(-c3ncc(F)c(S(C)=O)n3)c3cc(Cl)cnc32)cc1
5-chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine
On1nnc2cccnc21
HOAt
CCN(C(C)C)C(C)C
iPr2NEt
CN1CCC(N)C1=O
3-amino-1-methylpyrrolidin-2-one

الكواشف

لا شيء

المذيبات

CN(C)C=O.ClCCl
DCM DMF
C1CCOC1
THF
CC(=O)N(C)C
DMA

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

الإجراء التجريبي

3-amino-1-methylpyrrolidin-2-one, DMA, 140° C. microwave; (b) LiOH, THF, microwave, 120° C. (c) EDCI, HOAt, iPr2NEt, DCM-DMF (2:1).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08829007B2uspto-grants-2014_09