Di-tert-butyl dicarbonate → HCID 69317257, compound

HRID 1792155Notes

Reaction equation

HRID 1792155 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-dd257e48db34464b8c956bd6616382ef
Source dataset
uspto-grants-2006_07
Patent number
US07074939B2

Reaction notes

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