6-Azaindole → HCID 57985922, compound

HRID 1869203Notes

Reaction equation

HRID 1869203 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C([Mg]Cl)(C)C.[CH2:15]([O:17][C:18](=[O:32])[C:19](=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:16]>C1COCC1.[Cl-].[Cl-].[Zn+2]>[CH2:23]([O:22][C:20](=[O:21])[CH:19]([CH:25]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:3]1[C:4]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[NH:1][CH:2]=1)[C:18]([O:17][CH2:15][CH3:16])=[O:32])[CH3:24]

Participants

6

Reactant 3

HCID 92196-AzaindoleHCID 94751Diethyl (phenylmethylene)malonateHCID 178418918HCID 178418918, compound

Product 1

HCID 57985922HCID 57985922, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a RT solution of 1H-pyrrolo[2,3-c]pyridine (595 mg, 5.04 mmol) in THF (20 mL) was added i-PrMgCl (1.5 M in THF, 5.0 mL, 7.6 mmol) followed by ZnCl2 (1M in Et2O, 7.6 mL). The resulting mixture was stirred at RT for 5 min then a solution of 2-benzylidene-malonic acid diethyl ester (2.2 mL, 10 mmol) in THF (20 mL) was added dropwise. The mixture was stirred at RT for 1 hour, quenched by addition of a saturated solution of NH4Cl, and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (DCM/MeOH/NH4OH), affording 2-[Phenyl-(1H-pyrrolo[2,3-c]pyridin-3-yl)-methyl]-malonic acid diethyl ester (0.33 g, 18% yield).

Workup

  1. stirringThe mixture was stirred at RT for 1 hour
  2. customquenched by addition of a saturated solution of NH4Cl
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-d11de6c7ac914a4f94fb00c1720c8e0a
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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