2-Fluoropyridine-3-boronic acid → HCID 15603654, compound

HRID 2250356Notes

Reaction equation

HRID 2250356 reaction equation
Cl[C:2]1[C:3]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[CH:4][C:5]2[N:6]([C:8](=[O:22])[N:9]([CH2:11][C:12]3[CH:13]=[N:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=3)[N:10]=2)[N:7]=1.[F:30][C:31]1[C:36](B(O)O)=[CH:35][CH:34]=[CH:33][N:32]=1.ClC1C=CC(C2C(C3C=CC=CC=3)=NN3C(=O)N(CC4C=NC(C(F)(F)F)=CC=4)N=C3C=2)=CC=1>>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([C:3]2[C:2]([C:36]3[C:31]([F:30])=[N:32][CH:33]=[CH:34][CH:35]=3)=[N:7][N:6]3[C:8](=[O:22])[N:9]([CH2:11][C:12]4[CH:13]=[N:14][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:17]=4)[N:10]=[C:5]3[CH:4]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 27832702-Fluoropyridine-3-boronic acidHCID 15603653HCID 15603653, compoundHCID 58772593HCID 58772593, compound

Product 1

HCID 15603654HCID 15603654, compoundYield 42%

Procedure

The title compound (41 mg, 42%) as a yellow solid was prepared from 6-chloro-7-(4-chlorophenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (88 mg, 0.2 mmol) and 2-fluoropyridin-3-ylboronic acid (56 mg, 0.4 mmol) according to the procedures described for 7-(4-chlorophenyl)-6-phenyl-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (Example 9). LC/MS (method A): retention time=3.38 min, (M+H)+=501. 1H NMR (CDCl3, 400 MHz): δ 8.84 (s, 1H), 8.14 (d, J=1.96 Hz, 1H), 7.97-8.01 (m, 1H), 7.68-7.76 (m, 2H), 7.46 (s, 1H), 7.34 (d,J=8.56 Hz, 2H), 7.04 (d,J=8.56 Hz, 2H), 6.89 (dd,J=8.56, 2.93 Hz, 1H), 5.34 (s, 2H).

Sources & evidence

ORD record
ord-eefb0cadf1d0491fab04370a7faf830e
Source dataset
uspto-grants-2008_01
Patent number
US07317012B2

Reaction notes

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