6-(5,5-Dimethyl[1,3,2]dioxaborinan-2-yl)-2-fluorobenzonitrile → 5-(4-Fluorophenyl)-2-trifluoromethyl[1,8]naphthyridine

HRID 1061837Notes

Reaction equation

HRID 1061837 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[N:13][C:14]([C:18]([F:21])([F:20])[F:19])=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1OS(C(F)(F)F)(=O)=O.CC1(C)COB(C2C(F)=C(C=CC=2)C#N)OC1.CC1(C)COB(C2C(C#N)=C(F)C=CC=2)OC1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][N:11]=[C:12]3[C:17]=2[CH:16]=[CH:15][C:14]([C:18]([F:20])([F:19])[F:21])=[N:13]3)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 116802486-(5,5-Dimethyl[1,3,2]dioxaborinan-2-yl)-2-fluorobenzonitrileHCID 116943293-(5,5-Dimethyl[1,3,2]dioxaborinan-2-yl)-2-fluorobenzonitrileHCID 86594178Trifluoromethanesulfonic acid 2-fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenyl ester

Product 1

HCID 98791365-(4-Fluorophenyl)-2-trifluoromethyl[1,8]naphthyridine

Procedure

In the attempted coupling of trifluoromethanesulfonic acid 2-fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenyl ester (30.0 mg, 0.068 mmol) with a 1:1 mixture of 3-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)-2-fluorobenzonitrile and 6-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)-2-fluorobenzonitrile (34.4 mg) following the procedure described in Example 35 part c), none of the expected product was obtained. Instead, the triflate was reduced, affording 5-(4-fluorophenyl)-2-trifluoromethyl[1,8]naphthyridine (13.9 mg, 42%). δH (360 MHz, CDCl3) 7.27-7.31 (2H, m), 7.46-7.50 (2H, m), 7.55 (1H, d, J 4.6), 7.82 (1H, d, J 8.4), 8.49 (1H, d, J 8.8), 9.27 (1H, d, J 4.6). m/z (ES+) 293 [MH]+.

Sources & evidence

ORD record
ord-ad20db1e7c3143e5b3d85b944987f22e
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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