Sodium Carbonate → 3-(5-amino-1-benzothien-2-yl)-5-(2H-tetrazol-5-yl)pyridin-2-amine

HRID 2199609Notes

Reaction equation

I[C:2]1[C:3]([NH2:13])=[N:4][CH:5]=[C:6]([C:8]2[N:9]=[N:10][NH:11][N:12]=2)[CH:7]=1.CC1(C)C(C)(C)OB([C:22]2[S:26][C:25]3[CH:27]=[CH:28][C:29]([NH2:31])=[CH:30][C:24]=3[CH:23]=2)O1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[NH2:31][C:29]1[CH:28]=[CH:27][C:25]2[S:26][C:22]([C:2]3[C:3]([NH2:13])=[N:4][CH:5]=[C:6]([C:8]4[N:9]=[N:10][NH:11][N:12]=4)[CH:7]=3)=[CH:23][C:24]=2[CH:30]=1

Participants

Conditions

Temperature: 40 °C

Procedure

The reaction mixture of 3-iodo-5-(2H-tetrazol-5-yl)pyridin-2-amine (288 mg, 1.0 mmol, 1 eq), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-5-amine (330 mg, 1.2 eq), triphenylphosphine (53 mg, 0.2 eq), and palladium diacetate (22 mg, 0.1 eq) in dioxane (3 mL) and aqueous sodium carbonate (2 M, 2 mL, 4 eq) under nitrogen atmosphere was vigorously stirred and heated at 40° C. for 30 minutes. The mixture was then partitioned between aqueous ammonium chloride and THF-EtOAc (1:10). The organic layer was isolated and dried with anhydrous sodium sulfate. The upper solution was concentrated down with silica gel. Upon a gradient column chromatography (EtOAc to MeOH-EtOAc 1:10) 3-(5-amino-1-benzothien-2-yl)-5-(2H-tetrazol-5-yl)pyridin-2-amine was obtained in the amount of 5 mg.

Workup

customThe mixture was then partitioned between aqueous ammonium chloride and THF-EtOAc (1:10)
customThe organic layer was isolated
dry with materialdried with anhydrous sodium sulfate
concentrationThe upper solution was concentrated down with silica gel

Sources & evidence

ORD record: ord-0f8aa65447864a3d80e239e9ad57f9d9
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359336B2

Reaction notes

Loading…