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

HRID 1928591Notes

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-89e129476c8e4cdd827258aeaced4642
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183381B2

Reaction notes

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