Methyl 2-(6-bromo-8-phenylimidazo[1,2-a]pyridin-2-yl)acetate → Methyl 2-(6-(5-(isopropylamino)thiazol-2-yl)-8-phenylimidazo[1,2-a]pyridin-2-yl)acetate

HRID 2197563Notes

Reaction equation

HRID 2197563 reaction equation
C(N([C:12]1[S:13][C:14](B2OC(C)(C)C(C)(C)O2)=[CH:15][N:16]=1)C(=O)OC(C)(C)C)(C)C.Br[C:27]1[CH:28]=[C:29]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:30]2[N:31]([CH:33]=[C:34]([CH2:36][C:37]([O:39][CH3:40])=[O:38])[N:35]=2)[CH:32]=1>>[CH:34]([NH:35][C:14]1[S:13][C:12]([C:27]2[CH:28]=[C:29]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:30]3[N:31]([CH:33]=[C:34]([CH2:36][C:37]([O:39][CH3:40])=[O:38])[N:35]=3)[CH:32]=2)=[N:16][CH:15]=1)([CH3:36])[CH3:33]

Participants

3

Reactant 2

HCID 58207940Methyl 2-(6-bromo-8-phenylimidazo[1,2-a]pyridin-2-yl)acetateHCID 58688452Tert-butyl isopropyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazol-2-yl)carbamate

Product 1

HCID 58207962Methyl 2-(6-(5-(isopropylamino)thiazol-2-yl)-8-phenylimidazo[1,2-a]pyridin-2-yl)acetate

Procedure

Prepared in an similar fashion as Example 34, step #4 from tert-butyl isopropyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazol-2-yl)carbamate and Methyl 2-(6-bromo-8-phenylimidazo[1,2-a]pyridin-2-yl)acetate. LCMS 407.4, HPLC Tr 2.02 min (Conditions C).

Workup

  1. customLCMS 407.4, HPLC Tr 2.02 min (Conditions C)

Sources & evidence

ORD record
ord-b7969f992e474edcad46e594a433ea6e
Source dataset
uspto-grants-2012_12
Patent number
US08338604B2

Reaction notes

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