2-Fluoropyridine-4-boronic acid → HCID 17953061, compound

HRID 1373808Notes

Reaction equation

HRID 1373808 reaction equation
Br[C:2]1[C:3]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[N:4][N:5]2[C:10]([NH:11][CH:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=[CH:7][C:6]=12.[F:24][C:25]1[CH:30]=[C:29](B(O)O)[CH:28]=[CH:27][N:26]=1>>[CH:12]1([NH:11][C:10]2[N:5]3[N:4]=[C:3]([C:17]4[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=4)[C:2]([C:29]4[CH:28]=[CH:27][N:26]=[C:25]([F:24])[CH:30]=4)=[C:6]3[CH:7]=[CH:8][CH:9]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 27833962-Fluoropyridine-4-boronic acidHCID 69447740HCID 69447740, compound

Product 1

HCID 17953061HCID 17953061, compoundYield 72%

Procedure

In a similar manner to that in Example 28, from 3-bromo-N-cyclopentyl-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-amine (240 mg, 0.64 mmol) and 2-fluoropyridin-4-ylboronic acid (271 mg, 1.92 mmol) after heating to 100° C. for 1.5 hours was formed N-cyclopentyl-2-(4-fluorophenyl)-3-(2-fluoro-4-pyridinyl)pyrazolo[1,5-α]pyridin-7-amine (180 mg, 72%) as a greenish solid. 1H NMR (CDCl3): δ 8.12 (d, 1H), 7.56 (m, 2H), 7.27 (m, 1H), 7.13–7.02 (m, 4H), 6.90 (s, 1H), 6.05–6.01 (m, 2H), 4.02 (m, 1H), 2.16 (m, 2H), 1.86–1.68 (m, 6H); 19F NMR (CDCl3) δ −68.65, −113.06; MS m/z 391 (M+1).

Sources & evidence

ORD record
ord-59d240f51c4c48e782dd296eaea76a9e
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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