Toluene → HCID 67689969, compound

HRID 2393435Notes

Reaction equation

HRID 2393435 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][CH:19]=[N: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>>[CH2:27]([O:26][C:24](=[O:25])[CH:29]=[CH:49][C:10]1[C:11]2[C:12](=[CH:13][N:14]=[C:15]([N:17]3[CH:21]=[N:20][CH:19]=[N:18]3)[CH:16]=2)[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:9]=1)[CH3:28]

Participants

4

Reactant 3

HCID 1140TolueneHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 86753093HCID 86753093, compound

Product 1

HCID 67689969HCID 67689969, compoundYield 96%

Procedure

A solution of 1-tert-butyloxycarbonyl-3-formyl-5-(1,2,4-triazol-1-yl)pyrrolo[2,3-c]pyridine (1.5 g, 4.8 mmol) and (carboethoxymethylene)triphenylphosphorane (2.0 g, 5.8 mmol) in toluene (30 mL) was heated at 80° C. under nitrogen for 90 min. The mixture was allowed to cool and the solvent was evaporated in vacuo. The residue was chromatographed on silica eluting with 20% EtOAc in DCM to give a colourless solid. This was triturated with ether and the solid rechromatographed on silica with 20% EtOAc in DCM to give the title compound (1.77 g, 96%) as a colourless solid. mp 178°-181° C. 1H NMR (360 MHz, CDCl3) δ 1.37 (3H, t, J=7.1Hz), 1.73 (9H, s), 4.31 (2H, q, J=7.1Hz), 6.59 (1H, d, J=16.2Hz), 7.81 (1H, d, J=16.2Hz), 8.03 (1H, s), 8.14 (1H, s), 8.30 (1H, s), 9.21 (1H, s) and 9.26 (1H, br s).

Workup

  1. temperatureto cool
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was chromatographed on silica eluting with 20% EtOAc in DCM
  4. customto give a colourless solid
  5. customThis was triturated with ether
  6. customthe solid rechromatographed on silica with 20% EtOAc in DCM

Sources & evidence

ORD record
ord-47f465d6b643433fb56b8cf9eae78397
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

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