5-Indolylboronic acid → 4-(5-(6-aminopyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzamide

HRID 85020노트

반응식

HRID 85020 반응식
[NH:1]1[C:9]2C(=CC(B(O)O)=CC=2)C=C1.Br[C:14]1[CH:15]=[C:16]2C(I)=C[N:20](S(C3C=CC(C)=CC=3)(=O)=O)[C:17]2=[N:18][CH:19]=1.CC1(C)C(C)(C)OB(C2C=CC(N)=NC=2)[O:36]1.COC1C=C(B(O)O)C=C(OC)C=1OC.Br[C:66]1[CH:67]=[C:68]2[C:74]([C:75]3[CH:76]=[C:77]4[C:81](=[CH:82][CH:83]=3)NC=C4)=[CH:73][N:72](S(C3C=CC(C)=CC=3)(=O)=O)[C:69]2=[N:70][CH:71]=1>>[NH2:20][C:17]1[N:18]=[CH:19][C:14]([C:66]2[CH:67]=[C:68]3[C:74]([C:75]4[CH:83]=[CH:82][C:81]([C:9]([NH2:1])=[O:36])=[CH:77][CH:76]=4)=[CH:73][NH:72][C:69]3=[N:70][CH:71]=2)=[CH:15][CH:16]=1

참가 물질

6

반응물 5

HCID 27343615-Indolylboronic acidHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 497590665-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 667791765-bromo-3-(1H-indol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 462343524-(5-(6-aminopyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzamide

실험 절차

Compound AE was prepared by a method analogous to that described in Example 1 by substituting 4-carbamoylphenylboronic acid for 1H-indol-5-ylboronic acid in the reaction with Intermediate A and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine for 3,4,5-trimethoxyphenylboronic acid in the reaction with Intermediate B. HPLC retention time: 1.13 minutes. MS ESI (m/z): 330.4 (M+H)+, calc. 329.

후처리

  1. customCompound AE was prepared by a method analogous to

출처 및 근거

ORD 기록
ord-624d072b4b5a4c91a43b83c2185fe3f9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846909B2

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