Potassium Carbonate → 4-(2-(4-Methylthiazol-2-ylamino)pyridin-4-yloxy)benzonitrile

HRID 910892Notes

Reaction equation

HRID 910892 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.F[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[C:12]([O:14][C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 178431958HCID 178431958, compound

Product 1

HCID 248271074-(2-(4-Methylthiazol-2-ylamino)pyridin-4-yloxy)benzonitrileYield 22.2%

Procedure

Following the method of Example 1, Step D, 2-(4-methylthiazol-2-ylamino)pyridin-4-ol (0.100 g, 0.483 mmol), 4-fluorobenzonitrile (0.064 g, 0.531 mmol) and potassium carbonate (0.167 g, 1.21 mmol) were reacted to provide 4-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzonitrile (0.033 g; 20.0% yield) as white solid. 1H NMR (CDCl3) δ 8.27 (d, 1H), 7.72 (m, 1H), 7.70 (m, 1H), 7.18 (m, 1H), 7.16 (m, 1H), 6.52 (dd, 1H), 6.49 (m, 1H), 6.38 (s, 1H), 2.28 (d, 3H). HPLC (5 to 95) Rt=2.69 min; Mass spectrum (esi) m/z=309 (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-bd92d5a53f3241dba2fb04fbb2c0bf3a
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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