3-(p-Toluenesulfonylamino)phenylboronic acid pinacol ester → N-(5-(3-(4-methylphenylsulfonamido)phenyl)thiazolo[5,4-b]pyridin-2-yl)acetamide

HRID 2077542Notes

Reaction equation

HRID 2077542 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14](B3OC(C)(C)C(C)(C)O3)[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[C:28]1[N:33]=[C:32]2[S:34][C:35]([NH:37][C:38](=[O:40])[CH3:39])=[N:36][C:31]2=[CH:30][CH:29]=1>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([C:28]3[N:33]=[C:32]4[S:34][C:35]([NH:37][C:38](=[O:40])[CH3:39])=[N:36][C:31]4=[CH:30][CH:29]=3)[CH:15]=[CH:16][CH:17]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 162177213-(p-Toluenesulfonylamino)phenylboronic acid pinacol esterHCID 56763853N-(5-Bromothiazolo[5,4-b]pyridin-2-yl)acetamide

Product 1

HCID 57585121N-(5-(3-(4-methylphenylsulfonamido)phenyl)thiazolo[5,4-b]pyridin-2-yl)acetamide

Procedure

This compound was made using 4-methyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzenesulfonamide and N-(5-bromothiazolo[5,4-b]pyridin-2-yl)acetamide and following the procedure in Example 146, Method N, step 2 above. MS (ESI pos. ion) m/z: 439. Calculated exact mass for C21H18N4O3S2 438.

Sources & evidence

ORD record
ord-132fef724e1742b795ba27e7161ea7d0
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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