5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine → HCID 59592988, compound

HRID 2262301Notes

Reaction equation

HRID 2262301 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9](I)=[C:8]([CH3:12])[C:6]=2[N:7]=1.[OH:19][CH2:20][CH2:21][NH:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[CH:27]=1)(=[O:25])=[O:24].[NH:35]1[C:43]2[C:38](=[CH:39][C:40](B3OC(C)(C)C(C)(C)O3)=[CH:41][N:42]=2)[CH:37]=[CH:36]1>>[CH3:12][C:8]1[C:6]2[N:7]=[C:2]([C:40]3[CH:39]=[C:38]4[CH:37]=[CH:36][NH:35][C:43]4=[N:42][CH:41]=3)[N:3]=[C:4]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[C:5]=2[S:10][C:9]=1[C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([S:23]([NH:22][CH2:21][CH2:20][OH:19])(=[O:25])=[O:24])[CH:27]=1

Participants

4

Reactant 3

HCID 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 44119345{3-[(2-Hydroxyethyl)sulfamoyl]phenyl}boronic acidHCID 595928802-Chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-d]pyrimidine

Product 1

HCID 59592988HCID 59592988, compound

Procedure

2-Chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-d]pyrimidine (50 mg) was coupled to N-(2-hydroxyethyl)-3-boronobenzene sulfonamide, and then reacted with 7-azaindole-5-boronic acid pinacol ester via General Procedure F. The product was purified by reverse phase HPLC to yield 17.7 mg of 423. MS (Q1) 551.1 (M)+

Workup

  1. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-9382fd9301254cc9b06b59d468db1961
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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