Di-tert-butyl dicarbonate → HCID 69317257, compound

HRID 2218225Notes

Reaction equation

HRID 2218225 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[C:6]([S:11][CH3:12])[CH:5]=2.[O:13](C(OC(C)(C)C)=O)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=O>CC#N.CN(C1C=CN=CC=1)C>[C:17]([O:16][C:14]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([S:11][CH3:12])[CH:5]=2)[CH:10]=[C:2]1[CH3:1])=[O:13])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 22034358HCID 22034358, compound

Product 1

HCID 69317257HCID 69317257, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

2-Methyl-6-methylthioindole (13.9 g) prepared according to Allais A. et al. Eur. J. Med. Chem.—Chim. Ther. (1975), 10(2), 187-99, was dissolved in CH3CN (150 mL) followed by the addition of (BOC)2O (18 g) with 480 mg DMAP. After 5 h the mixture was evaporated to dryness and the resulting 2-methyl-6-methylsulfanyl-indole-1-carboxylic acid tert-butyl ester was purified by chromatography over silica gel.

Workup

  1. customAfter 5 h the mixture was evaporated to dryness
  2. customthe resulting 2-methyl-6-methylsulfanyl-indole-1-carboxylic acid tert-butyl ester was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-c62120c3bb7148aeb8413a9f94f60362
Source dataset
uspto-grants-2008_08
Patent number
US07410994B2

Reaction notes

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