Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate → tert-Butyl 4-(2-(hydroxymethyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 1772647Notes

Reaction equation

HRID 1772647 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.[C:19]([N:26]1[CH2:31][CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH2:28][CH2:27]1)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>>[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:29]3[CH2:30][CH2:31][N:26]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:27][CH:28]=3)[N:7]2[CH:8]=1

Participants

3

Reactant 2

HCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 117727888(5-Bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-yl)methanol

Product 1

HCID 117733768tert-Butyl 4-(2-(hydroxymethyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Procedure

Compound 1e was subjected to Suzuki coupling reaction conditions with N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester using the method described in Example 1, Step G to obtain compound 26a. Mass Spectrum (LCMS, ESI pos.) Calcd. for C21H29N5O4: 416.2 (M+H). Found 416.3.

Sources & evidence

ORD record
ord-13f616338bc24f578a0397b79d07fef6
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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