N,N'-Dimethylethylenediamine → 1-(4-Chlorophenyl)-1H-pyrrolo[2,3-c]pyridine

HRID 1486822Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH:8]=2)[CH:3]=[CH:2]1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1.CNCCNC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Cu]I>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([N:1]2[C:9]3=[CH:8][N:7]=[CH:6][CH:5]=[C:4]3[CH:3]=[CH:2]2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 150 °C

Procedure

6-Azaindole (5.00 g, 42.3 mmol) was dissolved in DMF (150 mL) under nitrogen and 1-chloro-4-iodo-benzene (12.2 g, 50.8 mmol), N,N′-dimethylethylenediamine (911 uL, 8.46 mmol), K3PO4 (18.9 g, 88.9 mmol) and CuI (806 mg, 4.23 mmol) were added. The reaction mixture was heated at 150° C. for 18 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was suspended in 1M aq Na2CO3 (250 mL) and extracted into DCM (2×250 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography to give the title compound as a yellow solid (8.58 g, 88.6%). LCMS (ES+): 229.1 [MH]+. HPLC: Rt 4.48 min, 98.6% purity.

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated in vacuo
extractionextracted into DCM (2×250 mL)
dry with materialThe combined organic fractions were dried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-ae685789ab95441f8748070d52557965
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428498B2

Reaction notes

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