Diethyl Ether → Potassium 5'-methyl-5-(thiazol-2-yl)-[2,3'-bipyridine]-4-carboxylate

HRID 2047604Notes

Reaction equation

HRID 2047604 reaction equation
C[C:2]1([C:18]2[S:19][CH:20]=[CH:21][N:22]=2)[CH:7]=[N:6][C:5]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]1[C:14]([O:16]C)=[O:15].[CH3:23][Si](C)(C)[O-].[K+:28].C(OCC)C>O1CCCC1>[CH3:23][C:12]1[CH:13]=[C:8]([C:5]2[CH:4]=[C:3]([C:14]([O-:16])=[O:15])[C:2]([C:18]3[S:19][CH:20]=[CH:21][N:22]=3)=[CH:7][N:6]=2)[CH:9]=[N:10][CH:11]=1.[K+:28]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 23668039Potassium trimethylsilanolateHCID 67334548Methyl 5-methyl-5-(1,3-thiazol-2-yl)-2,3'-bipyridine-4-carboxylate

Product 1

HCID 67333359Potassium 5'-methyl-5-(thiazol-2-yl)-[2,3'-bipyridine]-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-methyl-5-(1,3-thiazol-2-yl)-2,3′-bipyridine-4-carboxylate (7-3, 890 mg, 2.9 mmol, 1 equiv) in tetrahydrofuran (14.3 mL) was added potassium trimethylsilanolate (640 mg, 5.0 mmol, 1.75 equiv). The reaction mixture was stirred at room temperature for 1 hour. Ethyl ether (15 mL) was added and the precipitate was filtered to afford the title compound (7-4) as a white solid. ESI+MS[M+H]+C15H12N3O2S=298.1

Workup

  1. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-8e8e5f23e90e439a895e2bc4c22c4f12
Source dataset
uspto-grants-2013_11
Patent number
US08592457B2

Reaction notes

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