2-(Cyclopentyloxy)pyridine-3-boronic acid → 5-{4-[2-(Cyclopentyloxy)pyridin-3-yl]-2-fluorophenyl}pyrazin-2-amine

HRID 1523924Notes

Reaction equation

HRID 1523924 reaction equation
[CH:1]1([O:6][C:7]2[C:12](B(O)O)=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:24]=[CH:25][C:26]([NH2:29])=[N:27][CH:28]=2)=[C:19]([F:30])[CH:18]=1>>[CH:1]1([O:6][C:7]2[C:12]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[N:24]=[CH:25][C:26]([NH2:29])=[N:27][CH:28]=4)=[C:19]([F:30])[CH:18]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 567766852-(Cyclopentyloxy)pyridine-3-boronic acidHCID 903128885-(4-Bromo-2-fluorophenyl)pyrazin-2-amine

Product 1

HCID 903131745-{4-[2-(Cyclopentyloxy)pyridin-3-yl]-2-fluorophenyl}pyrazin-2-amine

Procedure

The title compound was prepared using methods analogous to those described in Example 369 using (2-(cyclopentyloxy)pyridin-3-yl)boronic acid and 5-(4-bromo-2-fluorophenyl)pyrazin-2-amine in Step B. MS (ESI): mass calcd. for C20H19FN4O, 350.15; m/z found, 351.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.62-8.58 (m, 1H), 8.19-8.15 (m, 1H), 8.12 (d, J=1.5, 1H), 8.00-7.90 (m, 1H), 7.69-7.63 (m, 1H), 7.48-7.40 (m, 2H), 6.98-6.92 (m, 1H), 5.59-5.50 (m, 1H), 4.68 (s, 2H), 2.03-1.89 (m, 2H), 1.89-1.70 (m, 4H), 1.71-1.55 (m, 2H).

Sources & evidence

ORD record
ord-ee5540e43ac44b10b1ccb70c2ed24edb
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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