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5-Indolylboronic acid → 5-(3-(4-aminophenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-amine

HRID 85017
Notes
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Reaction equation

HRID 85017 reaction equation
N1C2C(=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.NC1N=CC(B(O)O)=CC=1.COC1C=C(B(O)O)C=C(OC)C=1OC.Br[C:60]1[CH:61]=[C:62]2[C:68]([C:69]3[CH:70]=[C:71]4[C:75](=[CH:76][CH:77]=3)[NH:74]C=C4)=[CH:67][N:66](S(C3C=CC(C)=CC=3)(=O)=O)[C:63]2=[N:64][CH:65]=1>>[NH2:74][C:75]1[CH:76]=[CH:77][C:69]([C:68]2[C:62]3[C:63](=[N:64][CH:65]=[C:60]([C:14]4[CH:15]=[CH:16][C:17]([NH2:20])=[N:18][CH:19]=4)[CH:61]=3)[NH:66][CH:67]=2)=[CH:70][CH:71]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 27343615-Indolylboronic acidHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 22396308(6-Aminopyridin-3-yl)boronic acidHCID 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

Product 1

HCID 46234191
5-(3-(4-aminophenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-amine

Procedure

Compound Z was prepared by a method analogous to that described in Example 1 by substituting 4-aminophenylboronic acid for 1H-indol-5-ylboronic acid in the reaction with Intermediate A and 6-aminopyridin-3-ylboronic acid for 3,4,5-trimethoxyphenylboronic acid in the reaction with Intermediate B. HPLC retention time: 0.68 minutes. MS ESI (m/z): 302.4 (M+H)+, calc. 301.

Sources & evidence

ORD record
ord-e7f12de0469e4200be13ccd7905df23a
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846909B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes