Potassium Iodide → 5-(Prop-2-ynyloxy)-2-(1H-tetrazol-1-yl)pyridine

HRID 80640Notes

Reaction equation

[N:1]1([C:6]2[N:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:21](Cl)[C:22]#[CH:23]>O.CN(C)C=O>[CH2:23]([O:12][C:9]1[CH:8]=[CH:7][C:6]([N:1]2[CH:5]=[N:4][N:3]=[N:2]2)=[N:11][CH:10]=1)[C:22]#[CH:21]

Participants

Conditions

Temperature: 80 °C

Procedure

To a flask under N2 fitted with a reflux condenser was added 6-tetrazol-1-yl-pyridin-3-ol (2.25 g, 13.7 mmol) and N,N-dimethylformamide (8.2 mL). Potassium carbonate (3.79 g, 27.4 mmol, 2 eq.), potassium iodide (0.143 g, 0.86 mmol, 0.06 eq.) and propargyl chloride (1.98 mL, 17.9 mmol, 1.3 eq.) were added and heated at 80° C. for three hours. The reaction was cooled to room temperature and 10 mL of water was added to affect precipitation. The solid was filtered off, washed with water and dried overnight. The expected product was used in the next step without further purification. 1H NMR (DMSO-d6): δ 10.08 (1H, s), 8.36 (1H, d, J=3.0 Hz), 8.01 (1H, d, J=9 Hz), 7.79 (1H, dd, J=3.0, 9.0 Hz), 5.01 (2H, s), 3.71 (1H, s)

Workup

customTo a flask under N2 fitted with a reflux condenser
temperatureThe reaction was cooled to room temperature
customprecipitation
filtrationThe solid was filtered off
washwashed with water
customdried overnight
customThe expected product was used in the next step without further purification

Sources & evidence

ORD record: ord-ce9d9c8272e64273bd9172492037f2fc
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846675B2

Reaction notes

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