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-b]pyridazin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 718626Notes

Reaction equation

HRID 718626 reaction equation
Br[C:2]1[N:6]2[N:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]2=[N:4][C:3]=1[CH2:17][OH:18].[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:18][CH2:17][C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:9][CH:8]=[N:7][N:6]2[C:2]=1[C:29]1[CH2:30][CH2:31][N:26]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:27][CH:28]=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 117728706(3-Bromo-8-morpholinoimidazo[1,2-b]pyridazin-2-yl)methanol

Product 1

HCID 117733826tert-Butyl 4-(2-(hydroxymethyl)-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Procedure

Compound 14a (2.5 g, 8.0 mmol) was subjected to Suzuki coupling conditions with N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester as described in Example 38, Step A to obtain compound 41a as a white solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C21H29N5O4: 416.2 (M+H). found: 416.2.

Sources & evidence

ORD record
ord-d16f7425372f4a0ba2ddb53769f3be60
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

Loading…