Bromine → 3-Bromoacetyl-1-(tert-butoxycarbonyl)-indole

HRID 583780Notes

Reaction equation

HRID 583780 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:5]=1)(=[O:3])[CH3:2].[Br:20]Br>C1COCC1>[Br:20][CH2:2][C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 14593498tert-Butyl 3-acetyl-1H-indole-1-carboxylate

Product 1

HCID 223425383-Bromoacetyl-1-(tert-butoxycarbonyl)-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-acetyl-1-(tert-butoxycarbonyl)-indole, which may be prepared as described in Step (b) above, (0.01 mol), in THF at a temperature of about −80° C. to about 25° C. is added bromine (0.01 mol), and the mixture is stirred from about 5 minutes to about 24 hours. 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 an excess of an aqueous solution of sodium bisulfite or an aqueous solution of sodium thiosulfate. The organic layer is washed with water, then brine, dried over sodium sulfate, and rotary evaporated to give 3-bromoacetyl-1-(tert-butoxycarbonyl)-indole, which may be purified, if needed or desired, by chromatography on silica gel or crystallization.

Workup

  1. customReaction progress

Sources & evidence

ORD record
ord-cb3ee0135320474fbb69c2982597df39
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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