6-Methyl-1H-pyrrolo[2,3-b]pyridine

PREPARATION 58 6-Methyl-1 H-pyrrolo[2, 3-b]pyridine The title compound of Preparation 57 (1 .00 g, 6.55 mmol), 2, 4, 6-trimethyl-1 , 3, 5, 2, 4, 6- trioxatriborinane (1 .0 ml, 7.2 mmol) and potassium carbonate (2.72 g, 19.7 mmol) were suspended in 13 ml dimethoxyethane in a microwave reactor and submitted to three vacuum-argon cycles. [1 , 1 '-Bis(diphenylphosphino)ferrocene]-dichloropalladium (II) complex with dichloromethane (0.29 g, 0.33 mmol) was added and the resulting mixture was submitted to three further vacuum-argon cycles. The mixture was stirred at 120°C for 2h under microwave irradiation. The mixture was allowed to cool and was filtered through Celite, eluting with ethyl acetate. The filtrate was evaporated under reduced pressure and the residue was purified using the Isolera Purification System (ethyl acetate-hexane gradient, 0:100 rising to 50:50) to give 0.57 g (4.31 mmol, 65percent) of the title compound as a beige solid. Purity 98percent. The title compound of Preparation   57 (1.00 g, 6.55 mmol), 2, 4, 6-trimethyl-1, 3, 5, 2, 4, 6-trioxatriborinane (1.0 ml, 7.2 mmol) and potassium carbonate (2.72 g, 19.7 mmol) were suspended in 13 ml dimethoxyethane in a microwave reactor and submitted to three vacuum-argon cycles. [1, 1'-Bis(diphenylphosphino)ferrocene]-dichloropalladium (II) complex with dichloromethane (0.29 g, 0.33 mmol) was added and the resulting mixture was submitted to three further vacuum-argon cycles. The mixture was stirred at 120ºC for 2h under microwave irradiation. The mixture was allowed to cool and was filtered through Celite, eluting with ethyl acetate. The filtrate was evaporated under reduced pressure and the residue was purified using the Isolera Purification System (ethyl acetate-hexane gradient, 0:100 rising to 50:50) to give 0.57 g (4.31 mmol, 65percent) of the title compound as a beige solid. Purity 98percent. [0443] A solution of 50percent NaOH (0.573 g) was added to N-protected 6-methyl-7-azaindole (0.390 g, 1.43 mmol) in Ethanol (10 mL). After refluxed for 8 h, the mixture was concentrated and was extracted with CHCl(c) Step 3 A solution of 6-methyl-1 H-pyrrolo[2, 3-b]pyridine (1.07g, 8.1 mmol) in ethyl acetate (37ml_) at 0C was treated with mCPBA (2.1 g, 12.2mmol) then stirred at 0C for 40 mins. mCPBA (0.21g, 1.2mmol) was added at 0C then left to warm to r.t and stirred overnight. Saturated aqueous sodium bicarbonate was added and the organic layer was separated. The aqueous was extracted with ethyl acetate, the combined organic phase was washed with saturated sodium bicarbonate, brine then dried (Na2S04) and concentrated in vacuo. The aqueous layers were combined and extracted with 2-methyltetrahydrofuran and the combined extracts were dried (Na2S04) and concentrated in vacuo. The two crude products were dissolved in hot methanol, combined, preadsorbed onto diatomaceous earth and purified by FCC eluting with 0-10% MeOH / DCM to afford the title compound as a pale orange solid (0.57g, 48%) LCMS (Method 3): Rt 0.74 min, m/z 149.1 [MH+].

Molecular Weight:132.16
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:132.068748264
Monoisotopic Mass:132.068748264
Topological Polar Surface Area:28.7
Heavy Atom Count:10
Complexity:124
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes