Methanol → 3-Azidoacetyl-1-(tert-butoxycarbonyl)-indole

HRID 583781Notes

Reaction equation

HRID 583781 reaction equation
Br[CH2:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:6]=1)=[O:4].[N-:21]=[N+:22]=[N-:23].[Na+].O.CO>C1COCC1>[N:21]([CH2:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:6]=1)=[O:4])=[N+:22]=[N-:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 33557Sodium AzideHCID 223425383-Bromoacetyl-1-(tert-butoxycarbonyl)-indole

Product 1

HCID 108702993-Azidoacetyl-1-(tert-butoxycarbonyl)-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3-bromoacetyl-1-(tert-butoxycarbonyl)-indole, which may be prepared as described in Step (c) above, (0.01 mol), in THF is added a solution or suspension of sodium azide (0.01 to 0.05 mol) in THF, which optionally contains from 0% to 50% water or methanol, and the mixture is stirred. Reaction progress may be followed by TLC or HPLC. When a sufficient amount of desired product is formed, the mixture (or, optionally, the residue which is obtained after first rotary evaporating off the reaction solvent) is partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over sodium sulfate, and rotary evaporated to give 3-azidoacetyl-1-(tert-butoxycarbonyl)-indole, which may be purified, if needed or desired, by chromatography on silica gel or crystallization.

Workup

  1. additionis added
  2. customReaction progress

Sources & evidence

ORD record
ord-759db84804cb4f2ebd1c84a8a9f06604
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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