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

HRID 85019

Reaction equation

HRID 85019 reaction equation
[NH:1]1[C:9]2C(=CC(B(O)O)=CC=2)C=C1.BrC1C=C2C(I)=CN(S(C3C=CC(C)=CC=3)(=O)=[O:25])C2=NC=1.[NH2:34][C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][C:36]=1[O:44][CH3:45].COC1C=C(B(O)O)C=C(OC)C=1OC.Br[C:62]1[CH:63]=[C:64]2[C:70]([C:71]3[CH:72]=[C:73]4[C:77](=[CH:78][CH:79]=3)NC=C4)=[CH:69][N:68](S(C3C=CC(C)=CC=3)(=O)=O)[C:65]2=[N:66][CH:67]=1>>[NH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:62]2[CH:63]=[C:64]3[C:70]([C:71]4[CH:79]=[CH:78][C:77]([C:9]([NH2:1])=[O:25])=[CH:73][CH:72]=4)=[CH:69][NH:68][C:65]3=[N:66][CH:67]=2)=[CH:37][C:36]=1[O:44][CH3:45]

Participants

6

Reactant 5

HCID 27343615-Indolylboronic acidHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 497590665-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 57473274(4-Amino-3-methoxyphenyl)boronic acidHCID 667791765-bromo-3-(1H-indol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 462343514-(5-(4-amino-3-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzamide

Procedure

Compound AD 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 4-amino-3-methoxyphenylboronic acid for 3,4,5-trimethoxyphenylboronic acid in the reaction with Intermediate B. HPLC retention time: 1.46 minutes. MS ESI (m/z): 359.2 (M+H)+, calc. 358.

Workup

  1. customCompound AD was prepared by a method analogous to

Sources & evidence

ORD record
ord-8dc9cdbe77ea406da1841f3d77a4c1bd
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Linked notes

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