5-Indolylboronic acid → US9814704, Example 21

HRID 85016

Reaction equation

HRID 85016 reaction equation
N1C2C(=CC(B(O)O)=CC=2)C=[CH:2]1.Br[C:14]1[CH:15]=[C:16]2[C:22](I)=[CH:21][N:20](S(C3C=CC(C)=CC=3)(=O)=O)[C:17]2=[N:18][CH:19]=1.[CH3:34][N:35]([CH3:45])[C:36]1[N:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1.COC1C=C(B(O)O)C=C(OC)C=1OC.Br[C:62]1[CH:63]=[C:64]2C(C3C=C4C(=CC=3)NC=C4)=[CH:69][N:68](S(C3C=CC(C)=CC=3)(=O)=O)[C:65]2=[N:66][CH:67]=1>>[NH:20]1[C:17]2=[N:18][CH:19]=[C:14]([C:39]3[CH:38]=[CH:37][C:36]([N:35]([CH3:45])[CH3:34])=[N:41][CH:40]=3)[CH:15]=[C:16]2[C:22]([C:62]2[CH:63]=[CH:64][C:65]([N:68]([CH3:69])[CH3:2])=[N:66][CH:67]=2)=[CH:21]1

Participants

6

Reactant 5

HCID 27343615-Indolylboronic acidHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 27632716-(Dimethylamino)pyridine-3-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 66778750US9814704, Example 21

Procedure

Compound X was prepared by a method analogous to that described in Example 1 by substituting 6-(dimethylamino)pyridin-3-ylboronic acid for 1H-indol-5-ylboronic acid in the reaction with Intermediate A and 6-(dimethylamino)pyridin-3-ylboronic acid for 3,4,5-trimethoxyphenylboronic acid in the reaction with Intermediate B. HPLC retention time: 1.17 minutes. MS ESI (m/z): 359.4 (M+H)+, calc. 358.

Sources & evidence

ORD record
ord-b62e0bb29ad04e869741604efd7ed71d
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Linked notes

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