Trimethylsilyldiazomethane → methyl 2-(tert-butoxy)-2-(6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate

HRID 1473209Notes

Reaction equation

HRID 1473209 reaction equation
[C:1]([O:5][CH:6]([C:10]1[N:15]([CH3:16])[C:14](=[O:17])[C:13]2[NH:18][CH:19]=[CH:20][C:12]=2[C:11]=1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].[Si](C=[N+]=[N-])(C)(C)[CH3:29]>CO>[C:1]([O:5][CH:6]([C:10]1[N:15]([CH3:16])[C:14](=[O:17])[C:13]2[NH:18][CH:19]=[CH:20][C:12]=2[C:11]=1[C:21]1[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=1)[C:7]([O:9][CH3:29])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 89463048HCID 89463048, compound

Product 1

HCID 89462627methyl 2-(tert-butoxy)-2-(6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetateYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the crude 2-(tert-butoxy)-2-(6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetic acid in Methanol (4 mL) was treated with TMS-diazomethane (1.481 mL, 2.96 mmol) and then resultant was allowed to stir at ambient temperature for 10 minutes. The mixture was concentrated and then purified on silica gel (0-10% MeOH/DCM) to give the desired product (67 mg, 41% yield over 2 two steps). 1H NMR (400 MHz, CHLOROFORM-d) d=9.71 (br. s., 1H), 7.47-7.32 (m, 3H), 7.31-7.23 (m, 1H), 7.19 (t, J=2.4 Hz, 1H), 6.10 (t, J=2.1 Hz, 1H), 5.39 (s, 1H), 3.82 (s, 3H), 3.72 (s, 3H), 2.44 (s, 3H), 0.94 (s, 9H); LC/MS (m/z) ES+=383 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified on silica gel (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-6aef8b6d51d242388d29fd5605227274
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

Loading…