5-Azaindole → HCID 57985923, compound

HRID 1869200Notes

Reaction equation

HRID 1869200 reaction equation
C([Mg]Cl)(C)C.[NH:6]1[C:14]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[CH:8]=[CH:7]1.[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:8]1[C:9]2[CH:10]=[N:11][CH:12]=[CH:13][C:14]=2[NH:6][CH:7]=1)[C:18]([O:17][CH2:15][CH3:16])=[O:32])[CH3:24]

Participants

6

Reactant 3

HCID 92205-AzaindoleHCID 94751Diethyl (phenylmethylene)malonateHCID 178418918HCID 178418918, compound

Product 1

HCID 57985923HCID 57985923, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
50 °C

Procedure

To a RT solution of isopropylmagnesium chloride (1.5 M in THF, 2.4 mL, 3.6 mmol) in THF (10 mL) was added a solution of 1H-pyrrolo[3,2-c]pyridine (350 mg, 3 mmol) in THF (3 mL), followed by a solution of ZnCl2 in THF (1 M, 3.4 mL). After stirring the resulting mixture at 50° C. for 5 minutes, 2-benzylidene-malonic acid diethyl ester (1.0 mL, 4.5 mmol) was added dropwise. The mixture was stirred at 50° C. for 3 h, cooled to RT, quenched by addition of a saturated solution of NH4Cl, and extracted 3 times with EtOAc. The combined extracts were dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (EtOAc), affording 2-[Phenyl-(1H-pyrrolo[3,2-c]pyridin-3-yl)-methyl]-malonic acid diethyl ester (0.77 g, 70% yield).

Workup

  1. stirringThe mixture was stirred at 50° C. for 3 h
  2. temperaturecooled to RT
  3. customquenched by addition of a saturated solution of NH4Cl
  4. extractionextracted 3 times with EtOAc
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified via flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-1073607b0ddd4c14b0d612f9e51c14a9
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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