Tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate → tert-Butyl 4-(5-(2-(hydroxymethyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

HRID 1772656Notes

Reaction equation

HRID 1772656 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:13]=[C:14]([CH2:16][OH:17])[N:15]=3)[CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1.CC1(C)C(C)(C)OB([C:26]2[CH:27]=[CH:28][C:29]([N:32]3[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]3)=[N:30][CH:31]=2)O1>>[OH:17][CH2:16][C:14]1[N:15]=[C:8]2[C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[N:12][CH:11]=[C:10]([C:26]3[CH:27]=[CH:28][C:29]([N:32]4[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]4)=[N:30][CH:31]=3)[N:9]2[CH:13]=1

Participants

3

Reactant 2

HCID 16217947Tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylateHCID 117728187(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 1d was subjected to Suzuki coupling reaction 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 method described in Example 1, Step G to obtain compound 30a. Mass Spectrum (LCMS, ESI pos.) Calcd. for C25H33N7O4: 496.2 (M+H). Found 496.3.

Sources & evidence

ORD record
ord-22e8970bcaf44415bfc376cf5ae7ec34
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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