Sodium Azide → 3-azidomethyl-9-(2,5-dichlorobenzyl)-9H-beta-carboline

HRID 992575Notes

Reaction equation

HRID 992575 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]=[CH:6][C:7]2[N:8]([CH2:17][C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=3[Cl:25])[C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3.[N-:26]=[N+:27]=[N-:28].[Na+]>C(O)C.C(Cl)Cl>[N:26]([CH2:3][C:4]1[N:5]=[CH:6][C:7]2[N:8]([CH2:17][C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=3[Cl:25])[C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N+:27]=[N-:28]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 18412229HCID 18412229, compound

Product 1

HCID 184122163-azidomethyl-9-(2,5-dichlorobenzyl)-9H-beta-carbolineYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 3-chloromethyl-9-(2,5-dichlorobenzyl)-9H-β-carboline hydrochloride (5.64 g, 15 mmol) and sodium azide (2.0 9, 30 mmol) in anhydrous ethanol (60 mL) was refluxed under nitrogen for 15 hours. The resulting suspension was cooled to room temperature, diluted with an equal volume of CH2Cl2, and washed with water (2×50 mL) and brine (2.5 mL), respectively. The organic extract was dried over anhydrous Na2SO4 and concentrated to give 5.70 grams (100%) of 3-azidomethyl-9-(2,5-dichlorobenzyl)-9H-β-carboline as a pale yellow solid. 1H NMR (CDCl3) δ8.75 (s, 1H), 8.20 (d, J=7.4 Hz, 1H), 8.04 (s, 1H), 7.58 (t,J=7.5 Hz, 1H), 7.32-7.40 (m, 3H), 7.20 (dd, J=9.6, 2.5 Hz, 1H), 6.53 (d, J=2.3 Hz,1H), 5.52 (s, 2H), 4.20 (s, 2H); MS monoisotopic mass (calculated) 381.1, MH+ (observed) 382.0, (MH+−N2) 354.2.

Workup

  1. temperaturewas refluxed under nitrogen for 15 hours
  2. washwashed with water (2×50 mL) and brine (2.5 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-12f4530331fd420d805b3e139a33dd7a
Source dataset
uspto-grants-2002_10
Patent number
US06469021B1

Reaction notes

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