1H-Pyrrolo[2,3-b]pyridine, 4-broMo-5-chloro-2-cyclopropyl- synthesis

5synthesis methods

Product Name:1H-Pyrrolo[2,3-b]pyridine, 4-broMo-5-chloro-2-cyclopropyl-
CAS Number:1187449-10-0
Molecular formula:C10H8BrClN2
Molecular Weight:271.54

2-Pyridinamine, 4-bromo-5-chloro-3-(2-cyclopropylethynyl)-

1187449-08-6
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1H-Pyrrolo[2,3-b]pyridine, 4-broMo-5-chloro-2-cyclopropyl-

1187449-10-0
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Yield:1187449-10-0 51%

Reaction Conditions:

with potassium tert-butylate in N,N-dimethyl-formamide at 35; for 10.5 h;Inert atmosphere;

Steps:

17

Description 17 (D17); ^bromo-S-chloro^-cyclopropyl-I H-pyrrolo^.S-blpyridine; To a stirred solution of 4-bromo-5-chloro-3-(cyclopropylethynyl)-2-pyridinamine (D16) (4.10 g, 15.0 mmol) in N,N-dimethylformamide (36 ml.) was added potassium tert- butoxide (4.214 g, 38.00 mmol) under argon. Reaction mixture heated to 35⁰C using an oil bath and allowed to stir for 10.5 h. Reaction mixture poured into water (300 ml_) and stirred in ether (400 ml_). Layers separated and aqueous portion extracted with ether (2 x 200 ml_). The combined extracts were dried over magnesium sulfate, filtered and solvent removed in vacuo yielding a pale brown solid. Solid recrystallised with ethyl acetate (50 ml_), solid filtered, washed and dried in oven yielding the title compound as an off-white solid (2.1 O g, 51 %).¹H NMR: (300 MHz, CDCI₃) δ 9.67 (s, 1 H), 8.16 (s, 1 H), 6.14 (s, 1 H), 2.08-2.00 (m, 1 H), 1.14-1.10 (m, 2H), 0.91-0.89 (m, 2H).

References:

WO2009/112473,2009,A1 Location in patent:Page/Page column 70

84249-14-9 Synthesis