[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)#[N:2].[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+].[Cl-].[Li+]>CN(C=O)C>[NH:22]1[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[N:2][N:24]=[N:23]1A mixture of 540 mg of 3-(4-cyanobutyl)-2-(3-pyridyl)indole, 173 mg of sodium azide, 142 mg of ammonium chloride and 5 mg of lithium chloride in 2 ml of DMF is heated at 120° overnight. After cooling the mixture is filtered and the filtrate diluted with ca. 25 ml of water. After the pH is adjusted to 10-11 with 3N NaOH, the solution is washed with ether to remove unreacted nitrile. The aqueous phase is adjusted to pH 5-6 with 2N HCl and extracted with ether. The ether extract is washed with water, dried over MgSO4 and concentrated in vacuo. The residue is purified to give 3-[4-(5-tetrazolyl)-butyl]-2-(3-pyridyl)indole.
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