[2-(Pyrrolidin-1-yl)pyridin-3-yl]boronic acid → HCID 90312717, compound

HRID 1524176Notes

Reaction equation

HRID 1524176 reaction equation
[N:1]1([C:6]2[C:11](B(O)O)=[CH:10][CH:9]=[CH:8][N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:23]=[CH:24][C:25]([NH2:28])=[N:26][CH:27]=2)=[C:18]([F:29])[CH:17]=1>>[F:29][C:18]1[CH:17]=[C:16]([C:11]2[C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[N:7][CH:8]=[CH:9][CH:10]=2)[CH:21]=[CH:20][C:19]=1[C:22]1[N:23]=[CH:24][C:25]([NH2:28])=[N:26][CH:27]=1

Participants

3

Reactant 2

HCID 46738016[2-(Pyrrolidin-1-yl)pyridin-3-yl]boronic acidHCID 903128885-(4-Bromo-2-fluorophenyl)pyrazin-2-amine

Product 1

HCID 90312717HCID 90312717, compound

Procedure

Title compound was prepared using methods analogous to those described in Example 377 using (2-(pyrrolidin-1-yl)pyridine-3-yl)boronic acid and 5-(4-bromo-2-fluorophenyl)pyrazin-2-amine in Step B. MS (ESI): mass calcd. for C19H18FN5, 335.15; m/z found, 336.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.61-8.56 (m, 1H), 8.22-8.17 (m, 1H), 8.12 (s, 1H), 7.97-7.88 (m, 1H), 7.45-7.38 (m, 1H), 7.29-7.23 (m, 1H), 7.21-7.14 (m, 1H), 6.75-6.67 (m, 1H), 4.67 (s, 2H), 3.28-3.10 (m, 4H), 1.87-1.73 (m, 4H).

Sources & evidence

ORD record
ord-a2015cd0537e495a9ff0e52800d8ddb0
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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