2-Fluoropyridine-4-boronic acid → HCID 10157930, compound

HRID 1373837Notes

Reaction equation

HRID 1373837 reaction equation
Br[C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[N:4][N:5]2[C:10](Cl)=[CH:9][CH:8]=[CH:7][C:6]=12.[F:19][C:20]1[CH:25]=[C:24](B(O)O)[CH:23]=[CH:22][N:21]=1>>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:3]2[C:2]([C:24]3[CH:23]=[CH:22][N:21]=[C:20]([F:19])[CH:25]=3)=[C:6]3[CH:7]=[CH:8][CH:9]=[C:10]([C:24]4[CH:23]=[CH:22][N:21]=[C:20]([F:19])[CH:25]=4)[N:5]3[N:4]=2)=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 27833962-Fluoropyridine-4-boronic acidHCID 86616860HCID 86616860, compound

Product 1

HCID 10157930HCID 10157930, compoundYield 34.4%

Procedure

In a similar manner to that in Example 28, from 3-bromo-7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridine (305 mg, 0.94 mmol) and 2-fluoropyridin-4-ylboronic acid (182 mg, 1.30 mmol) after heating to 100° C. for 1.5 hours was formed 2-(4-fluorophenyl)-3,7-bis(2-fluoropyridin-4-yl)pyrazolo[1,5-α]pyridine (90 mg, 24%). 1H NMR (CDCl3): δ 8.47 (d, 1H), 8.29 (d 1H), 7.89 (br d, 1H), 7.78 (d, 1H), 7.72 (s, 1H), 7.58 (dd, 2H), 7.44 (dd, 1H), 7.20 (br d, 1H), 7.15 (d, 1H), 7.13 (t, 2H), 7.05 (s, 1H); MS m/z 403 (M+1).

Sources & evidence

ORD record
ord-f0710ce80aa74d748f6ea476296eb011
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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