2-Chloroquinolin-6-ol → 3-(3-fluoro-4-(6-hydroxyquinolin-2-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one

HRID 1410577Notes

Reaction equation

HRID 1410577 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:18])[CH:14]=3)[N:9]=2)[CH:5]=[CH:4][C:3]=1[C:19]1[NH:23][C:22](=[O:24])[O:21][N:20]=1.ClC1C=CC2C(=CC=C(O)C=2)N=1.C(C1C=CC(B(O)O)=C([F:48])C=1)#N>>[F:48][C:7]1[CH:2]=[C:3]([C:19]2[NH:23][C:22](=[O:24])[O:21][N:20]=2)[CH:4]=[CH:5][C:6]=1[C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:18])[CH:14]=2)[N:9]=1

Participants

4

Reactant 3

HCID 221325772-Chloroquinolin-6-ol2×HCID 447552094-Cyano-2-Fluorophenylboronic AcidHCID 136078979HCID 136078979, compound

Product 1

HCID 1360789833-(3-fluoro-4-(6-hydroxyquinolin-2-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one

Procedure

Followed procedure described for Compound 20 in Example 20 starting from 2-chloroquinolin-6-ol (Intermediate 2) and 4-cyano-2-fluorophenylboronic acid. 1H NMR (DMSO-d6, 300 MHz): δ 10.22 (1H, s), 8.27-8.33 (2H, m), 7.97 (1H, d, J=9 Hz), 7.77-7.82 (2H, m), 7.39 (1H, dd, J=3, 9 Hz), 7.21 (1H, d, J=3 Hz) ppm. MS (ESI): m/z 324.0 [M+1]+.

Sources & evidence

ORD record
ord-00b0d1615282476fa6c8f03d8402dcf8
Source dataset
uspto-grants-2014_12
Patent number
US08921562B2

Reaction notes

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