Methanesulfonyl chloride → HCID 86594331, compound

HRID 2116727Notes

Reaction equation

HRID 2116727 reaction equation
[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[C:12]([CH2:16]O)[NH:13]2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].CS(Cl)(=O)=O.[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C>[N:25]([CH2:16][C:12]1[NH:13][C:14]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:19])[CH3:18])[CH:15]=2)=[N+:26]=[N-:27]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 59814778HCID 59814778, compound

Product 1

HCID 86594331HCID 86594331, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

[6-(tert-Butyl-dimethyl-silanyloxy)-1H-indol-2-yl]-methanol (2.0 g, 7.21 mmol) is dissolved in DMF (950 ml), cooled to 0° C. TEA (2.01 ml, 14.42 mmol) and MsCl (0.83 g, 7.21 mmol) are added. The mixture is stirred at room temperature for 1 hour. NaN3 (2.34 g, 34 mmol) is added. The reaction is stirred at room temperature for 1 hour and then 80° C. overnight. The mixture is cooled to room temperature, concentrated. The residue is purified by column chromatography (10% ethyl acetate in hexanes) to give 2-Azidomethyl-6-(tert-butyl-dimethyl-silanyloxy)-1H-indole (1.40 g, 64%). 1H NMR (400 MHz, DMSO-d6): δ 11.08 (s, 1H), 7.38 (d, 1H), 6.80 (s, 1H), 6.58 (m, 1H), 6.40 (s, 1H), 4.53 (d, 2H), 0.96 (s, 9H), 0.17 (s, 6H).

Workup

  1. stirringThe reaction is stirred at room temperature for 1 hour
  2. custom80° C. overnight
  3. temperatureThe mixture is cooled to room temperature
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9902b4e21d654c178b5288dd4e0dcbf1
Source dataset
uspto-grants-2008_10
Patent number
US07439249B2

Reaction notes

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