HCID 86759982, compound → HCID 69591774, compound

HRID 1795966Notes

Reaction equation

HRID 1795966 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][O:6][C:7]([C:9]1[CH:10]=[CH:11][N:12]2[C:17]=1[C:16](=[O:18])[N:15]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]([CH:26]=[O:27])=[N:13]2)=[O:8]>C(Cl)Cl>[CH3:5][O:6][C:7]([C:9]1[CH:10]=[CH:11][N:12]2[C:17]=1[C:16](=[O:18])[N:15]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]([CH:26]([OH:27])[CH2:1][CH3:2])=[N:13]2)=[O:8]

Participants

4

Reactant 2

HCID 86759982HCID 86759982, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 69591774HCID 69591774, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl magnesium bromide (1 M, 0.77 ml, 0.77 mmol) was added dropwise to a −78° C. solution of 3-benzyl-2-formyl-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-5-carboxylic acid methyl ester (0.12 g, 0.39 mmol) in CH2Cl2 (6.0 mL) over 45 min. The reaction mixture was stirred at −78° for 30 min, quenched with saturated NH4Cl (10 mL) and warmed to room temperature. The reaction mixture was extracted with CHCl3 (3×25 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 1/1 hexane/EtOAc to afford the title compound (0.070 g, 50%) as a solid: MS (ESI+) 342 (M++H).

Workup

  1. customquenched with saturated NH4Cl (10 mL)
  2. extractionThe reaction mixture was extracted with CHCl3 (3×25 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with 1/1 hexane/EtOAc

Sources & evidence

ORD record
ord-ca00112a27104de2a26ec63449000b3f
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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