Water → 5-(Azidomethyl)-1-(2-tetrahydropyranyl)indazole

HRID 1634080Notes

Reaction equation

Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)[N:7]=[CH:6]2.[N-:18]=[N+:19]=[N-:20].[Na+].O>CN(C=O)C>[N:18]([CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)[N:7]=[CH:6]2)=[N+:19]=[N-:20]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 5-(bromomethyl)-1-(2-tetrahydropyranyl)indazole (compound 108, 3.0 g, 10.2 mmol) in DMF (30 mL), was added with sodium azide (Aldrich, 2.64 g, 40.6 mmol) in one portion. The suspension was heated at 90° C. for 30 minutes and a yellow solution formed. After cooling to room temperature, the reaction mixture was poured into water (100 mL) and extracted with ether (2×150 mL). Combined organic layers were washed with brine, then dried (MgSO4). Evaporation of solvent gave the product (109) as a yellow oil (2.61 g, 99%). TLC Rf 0.63 (60:40 hexane-ethyl acetate); MS (electrospray) 258 (M+1); 1H NMR (CDCl3) δ2.03-2.15 (m, 2H), 2.55 (m, 1H), 3.72 (m, 1H), 4.02 (m, 1H), 4.52 (s, 1H), 5.71 (d, 1H, J=9.4 Hz), 7.32 (d, 1H, J=8.8 Hz), 7.56 (d, 1H, J=8.8 Hz), 7.63 (s, 1H), 8.00 (s, 1H).

Workup

customa yellow solution formed
temperatureAfter cooling to room temperature
extractionextracted with ether (2×150 mL)
washCombined organic layers were washed with brine
dry with materialdried (MgSO4)
customEvaporation of solvent

Sources & evidence

ORD record: ord-87cc1c41ea514314819961f9f059e80f
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506754B1

Reaction notes

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