Potassium Carbonate → tert-Butyl 4-(5-(2-(hydroxymethyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

HRID 1772640Notes

Reaction equation

HRID 1772640 reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][OH:12])[N:10]=[C:6]2[C:5]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[CH:29][C:30]([N:33]3[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]3)=[N:31][CH:32]=2)O1.C([O-])([O-])=O.[K+].[K+]>>[OH:12][CH2:11][C:9]1[N:10]=[C:6]2[C:5]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[N:4][CH:3]=[C:2]([C:27]3[CH:28]=[CH:29][C:30]([N:33]4[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]4)=[N:31][CH:32]=3)[N:7]2[CH:8]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 16217947Tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylateHCID 117727888(5-Bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-yl)methanol

Product 1

HCID 117733761tert-Butyl 4-(5-(2-(hydroxymethyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

Procedure

Compound 1e was subjected to Suzuki coupling conditions with tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate using the reaction conditions described in Example 1, Step G, and substituting K2CO3 as the base to obtain compound 23a. Mass Spectrum (LCMS, ESI pos.) Calcd. for C25H33N7O4: 496.3 (M+H). Found 496.3.

Workup

  1. customthe reaction conditions

Sources & evidence

ORD record
ord-ca519d05787145b6af9fc5d41e5d0487
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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