Tert-butyl N-[5-methoxy-2-(2-oxopropyl)phenyl]carbamate → 6-methoxy-2-methyl-1H-indole

HRID 2292779Notes

Reaction equation

HRID 2292779 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7](C(=O)C(N)=O)=[C:8]([CH3:19])[N:9]2CC2C=CC=CC=2)=[CH:5][CH:4]=1.C(OC(NC1C=C(OC)C=CC=1CC(=O)C)=O)(C)(C)C>>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([CH3:19])[NH:9]2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 10707784Tert-butyl N-[5-methoxy-2-(2-oxopropyl)phenyl]carbamateHCID 108057846-Methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-glyoxylic acid amide

Product 1

HCID 108447096-methoxy-2-methyl-1H-indoleYield 61%

Procedure

6-Methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-glyoxylic acid amide. Using the method in Example 9, Part C, 13.7 g 49 mmol) of 1-[2-(tert-butoxycarbonylamino)-4-methoxyphenyl]-2-propanone was reacted with 20 mL of trifluoroacetic and the product chromatographed on silica eluting with 20% EtOAc/hexane. There was obtained 4.8 g (61% yield) of crude 6-methoxy-2-methyl-1H-indole. By the method in Example 6, Part A, this maternal (30 mmol) was treated with 1.2 g (30 mmol) of 60% NaH/mineral oil and 3.6 mL of benzyl bromide in DHF to give after chromatography on silica (eluting with 25% EtOAc/hexane) 4.77 g (63% yield) of 6-methoxy-2-methyl-1-(phenylmethyl)-1H-indole. By the method in Example 16, Part C, 1.97 g (8 mmol) of 6-methoxy-2-methyl-1-(phenylmethyl)-1H-indole was reacted with 0.73 mL (8.4 mmol) of oxalyl chloride and then ammonia to give 0.875 g (24% yield) of 6-methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-glyoxylic acid amide from EtOAc, mp, 230°-234° C.

Workup

  1. customwas reacted with 20 mL of trifluoroacetic and the product
  2. customchromatographed on silica eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-3f93d82701464d5385250a72699dfb93
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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