Toluene → HCID 73503327, compound

HRID 2393447Notes

Reaction equation

HRID 2393447 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2=[CH:13][N:14]=[C:15]([N:17]3[CH:21]=[N:20][N:19]=[CH:18]3)[CH:16]=[C:11]2[C:10](C=O)=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24]([CH:29]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:26][CH2:27][CH3:28])=[O:25].[C:49]1(C)C=CC=CC=1>>[C:1]([O:5][C:6]([N:8]1[C:12]2=[CH:13][N:14]=[C:15]([N:17]3[CH:21]=[N:20][N:19]=[CH:18]3)[CH:16]=[C:11]2[C:10]([CH:49]=[CH:29][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 1140TolueneHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 18975311HCID 18975311, compound

Product 1

HCID 73503327HCID 73503327, compound

Procedure

A solution of 1-tert-butyloxycarbonyl-3-formyl-5-(1,2,4-triazol-4-yl)pyrrolo[2,3-c]pyridine (0.71 g, 2.3 mmol) and (carboethoxymethylene)triphenylphosphorane (0.95 g, 2.7 mmol) in toluene (25 mL) was heated at 80° C. under nitrogen for 2 hours. The mixture was allowed to cool and the solvent evaporated in vacuo. The residue was chromatographed on silica eluting with 20% EtOAC in DCM, followed by a gradient of 2 to 5% MeOH in DCM to afford ethyl 3-[1-tert-butyloxycarbonyl-5-(1,2,4-triazol-4-yl)pyrrolo[2,3-c]pyridin-3-yl]prop-2-enoate (0.93 g), contaminated with minor impurities, as a cream solid. 1H NMR (360 MHz, CDCl3) δ 1.38 (3H, t, J=7.1Hz), 1.73 (9H, s), 4.32 (2H, q, J=7.1Hz), 6.51 (1H, d, J=16.2Hz), 7.76 (1H, s), 7.80 (1H, d, J=15.7Hz), 8.09 (1H, s), 8.95 (2H, s) and 9.33 (1H, s). This was used without further purification.

Workup

  1. temperatureto cool
  2. customthe solvent evaporated in vacuo
  3. customThe residue was chromatographed on silica eluting with 20% EtOAC in DCM

Sources & evidence

ORD record
ord-6468a0dd574b4ad68c010cea029a5044
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

Loading…