Triethylamine → HCID 57893467, compound

HRID 1821840Notes

Reaction equation

Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:12])[NH:8][C:7]=12.C(N(CC)CC)C>CN(C)C=O.C(Cl)Cl.[Pd](Cl)Cl>[C:13]1([C:11]([C:9]2[NH:8][C:7]3=[CH:2][N:3]=[CH:4][CH:5]=[C:6]3[CH:10]=2)=[O:12])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

(7-Chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)(phenyl)methanone (Example 29) (1.09 g, 4.25 mmol), palladium(II)chloride (15.4 mg, 3 mol %) and triethylamine (1.3 mL) were combined in N,N-dimethylformamide (25 mL). The reaction mixture was heated at 60° C. under an atmosphere of hydrogen for 8 h, then at room temperature for an additional 16 h. The reaction mixture was diluted with methylene chloride (25 mL) and filtered through a pad of diatomaceous earth. Evaporation of the solvents provided 1.3 g of crude orange solid. Purification by chromatography (SiO2; 0-10% methanol in methylene chloride, 1400 mL) afforded phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (196 mg, 0.893 mmol, 21%) as an off-white solid: mp 245-247° C.; 1H NMR (300 MHz, CD3OD) δ 7.18 (1H, s), 7.55-7.63 (2H, m), 7.65-7.77 (2H, m), 7.95-8.04 (2H, m), 8.17 (1H, d, J=5.7 Hz), 8.87 (1H, s); ESI MS m/z 223 [C14H10N2O+H]+; HPLC (Method A) >99% (AUC), tR=13.4 min.

Workup

filtrationfiltered through a pad of diatomaceous earth
customEvaporation of the solvents
customprovided 1.3 g of crude orange solid
customPurification by chromatography (SiO2; 0-10% methanol in methylene chloride, 1400 mL)

Sources & evidence

ORD record: ord-71b08f066c8046c6bc594215c23bd895
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608627B2

Reaction notes

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