tert-butyl (2,4-dimethylphenyl)carbamate → HCID 23368800, compound

HRID 1901779Notes

Reaction equation

HRID 1901779 reaction equation
[CH2:1]([C:3]1NC2C([CH:11]=1)=CC(C)=CC=2)[CH3:2].[C:13]([O:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=1[CH3:28])=[O:19])([CH3:16])([CH3:15])[CH3:14].C([Li])(CC)C.C[O:35]N(C)C(=O)CC>>[C:13]([O:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=1[CH2:28][C:11](=[O:35])[CH2:3][CH2:1][CH3:2])=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 4

HCID 4935447tert-butyl (2,4-dimethylphenyl)carbamateHCID 11344007N-Methoxy-N-methylpropionamideHCID 20517183HCID 20517183, compoundHCID 178418400CID 53628100

Product 1

HCID 23368800HCID 23368800, compound

Procedure

2-Ethyl-5-methyl-1H-indole. Using methods described in Example 1, Part D, 11.05 g (0.05 mol) of N-tert-butoxycarbonyl-2,4-dimethylaniline was reacted with 81 mL of 1.3M sec-butyl lithium and 6.1 g (0.05 mol) of N-methoxy-N-methylpropanamide to give the crude 1-[2-(tert-butoxycarbonylamino)-5-methylphenyl)-2-pentanone. Treatment of this material with trifluoroacetic and crystallization from EtOAc/hexane gave 1.82 g (13% yield) of 2-ethyl-5-methyl-1H-indole, mp, 77°-78° C.

Sources & evidence

ORD record
ord-61596622ed0b4c96bf532ca05b0f841e
Source dataset
uspto-grants-1996_11
Patent number
US05578634

Reaction notes

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