2-(Tributylstannyl)pyrazine → HCID 10270477, compound

HRID 1061828Notes

Reaction equation

HRID 1061828 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.C([Sn](CCCC)(CCCC)[C:35]1[CH:40]=[N:39][CH:38]=[CH:37][N:36]=1)CCC>>[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][C:7]=1[C:35]1[CH:40]=[N:39][CH:38]=[CH:37][N:36]=1

Participants

3

Reactant 2

HCID 27373162-(Tributylstannyl)pyrazineHCID 86594178Trifluoromethanesulfonic acid 2-fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenyl ester

Product 1

HCID 10270477HCID 10270477, compoundYield 33.4%

Procedure

Trifluoromethanesulfonic acid 2-fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenyl ester (30.0 mg, 0.068 mmol) was coupled to 2-tributylstannylpyrazine (50.2 mg, 0.14 mmol) as described in Example 42, affording 5-(4-fluoro-3-pyrazin-2-ylphenyl)-2-trifluoromethyl[1,8]naphthyridine (8.4 mg, 33%). δH (360 MHz, CDCl3) 7.46 (1H, dd, J 10.5 and 8.4), 7.56-7.61 (1H, m), 7.63 (1H, d, J 4.2), 7.85 (1H, d, J 8.4), 8.24 (1H, dd, J 2.3 and 7.2), 8.55 (1H, d, J 8.8), 8.60 (1H, d, J 2.5), 8.68-8.69 (1H, m), 9.23 (1H, t, J 1.9), 9.30 (1H, d, J 4.6). m/z (ES+) 371 [MH]+.

Sources & evidence

ORD record
ord-68728eb1191b4f1b8851c6736bb8dd18
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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