(4-(N-(2-((tert-Butyldimethylsilyl)oxy)ethyl)sulfamoyl)phenyl)boronic acid → (E)-N-(2-((tert-Butyldimethylsilyl)oxy)ethyl)-4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)benzenesulfonamide

HRID 1772663Notes

Reaction equation

HRID 1772663 reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[N:10]=[C:6]2[C:5]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:4][CH:3]=1.[Si:29]([O:36][CH2:37][CH2:38][NH:39][S:40]([C:43]1[CH:48]=[CH:47][C:46](B(O)O)=[CH:45][CH:44]=1)(=[O:42])=[O:41])([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]>>[Si:29]([O:36][CH2:37][CH2:38][NH:39][S:40]([C:43]1[CH:48]=[CH:47][C:46]([C:2]2[N:7]3[CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]4[CH:22]=[CH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[N:14]=4)[N:10]=[C:6]3[C:5]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[N:4][CH:3]=2)=[CH:45][CH:44]=1)(=[O:42])=[O:41])([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]

Participants

3

Reactant 2

HCID 44119854(4-(N-(2-((tert-Butyldimethylsilyl)oxy)ethyl)sulfamoyl)phenyl)boronic acidHCID 117728505(E)-4-(5-Bromo-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-8-yl)morpholine

Product 1

HCID 131734677(E)-N-(2-((tert-Butyldimethylsilyl)oxy)ethyl)-4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)benzenesulfonamide

Procedure

Compound 2b was subjected to Suzuki coupling reaction conditions as described in Example 1, Step G, with (4-(N-(2-((tert-butyldimethylsilyl)oxy)ethyl)sulfamoyl)phenyl)boronic acid to obtain compound 33a. Mass Spectrum (LCMS, ESI pos.) Calcd. For C35H42N6O4SSi: 671.3 (M+H). Found 671.3.

Sources & evidence

ORD record
ord-9c48ccdb5876402f81ccaa06a62b0485
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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