Sodium Carbonate → 5-(5-Bromo-3-pyridyl)-1H-tetrazole

HRID 2199611Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[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:21]2[S:25][C:24]3[CH:26]=[CH:27][C:28]([NH2:30])=[CH:29][C:23]=3[CH:22]=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]>[N:12]1[NH:11][N:10]=[N:9][C:8]=1[C:6]1[CH:7]=[C:2]([C:21]2[S:25][C:24]3[CH:26]=[CH:27][C:28]([NH2:30])=[CH:29][C:23]=3[CH:22]=2)[CH:3]=[N:4][CH:5]=1.[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2[N:9]=[N:10][NH:11][N:12]=2)[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The reaction mixture of 3-bromo-5-(2H-tetrazol-5-yl)pyridine (226 mg, 1.0 mmol, 1 eq), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-5-amine (316 mg, 1.15 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 100° C. for three hours. It was then cooled to room temperature, filtered through a Buchner funnel, and rinsed with small amount of water and ethyl acetate. The filtrate was isolated and concentrated down with silica gel. Upon a gradient column chromatography (EtOAc to MeOH-EtOAc 1:4), 2-(5-(2H-tetrazol-5-yl)pyridin-3-yl)benzo[b]thiophen-5-amine was obtained as an orange colored solid in the amount of 92 mg while the starting material, 3-bromo-5-(2H-tetrazol-5-yl)pyridine was recovered in the amount of 90 mg.

Workup

temperatureIt was then cooled to room temperature
filtrationfiltered through a Buchner funnel
washrinsed with small amount of water and ethyl acetate
customThe filtrate was isolated
concentrationconcentrated down with silica gel

Sources & evidence

ORD record: ord-41dc2c2c35014a42b20ec36035e1afff
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359336B2

Reaction notes

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