1-Ethyl-1H-pyrazole-4-boronic acid, pinacol ester → (Rac)-[6-(1-ethyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-(7-fluoro-quinolin-6-yl)methanol

HRID 69262Notes

Reaction equation

HRID 69262 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][C:22]=3[F:23])[N:19]=[CH:18][CH:17]=[CH:16]4)[OH:12])=[CH:9][N:10]=2)[N:7]=1.[CH2:24]([N:26]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[N:27]1)[CH3:25]>>[CH2:24]([N:26]1[CH:30]=[C:29]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([CH:11]([C:13]4[CH:14]=[C:15]5[C:20](=[CH:21][C:22]=4[F:23])[N:19]=[CH:18][CH:17]=[CH:16]5)[OH:12])=[CH:9][N:10]=3)[N:7]=2)[CH:28]=[N:27]1)[CH3:25]

Participants

3

Reactant 2

HCID 113790451-Ethyl-1H-pyrazole-4-boronic acid, pinacol esterHCID 58147515(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(7-fluoroquinolin-6-yl)methanol

Product 1

HCID 57917373(Rac)-[6-(1-ethyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-(7-fluoro-quinolin-6-yl)methanol

Procedure

The title compound was prepared in analogy to Example 9 using (rac)-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-(7-fluoro-quinolin-6-yl)-methanol (Stage 174.3) instead of (rac)-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-imidazo[1,2-a]pyridin-6-yl-methanol (Stage 9.1) and 1-ethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole instead of 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (tR 3.38 min (conditions 3), MH+=389.2).

Sources & evidence

ORD record
ord-d7f904ccc0ad4ddaae456c28daa0dd8c
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

Loading…