Sodium Methoxide → 5-Bromo-4-methoxy-1H-pyrrolo[2,3-b]pyridine

HRID 1693695Notes

Reaction equation

[Br:1][C:2]1[C:3](Cl)=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:12][O-:13].[Na+]>CO>[Br:1][C:2]1[C:3]([O:13][CH3:12])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 175 °C

Procedure

5-Bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (500 mg, 2.16 mmol) was combined with sodium methoxide (583 mg, 10.8 mmol) and suspended in anhydrous methanol (10 mL). The reaction was heated in the microwave to 175° C. for 4 h. The reaction mixture was concentrated and purified by flash silica gel chromatography using a gradient of (ethyl acetate/methanol 9:1) in hexanes to afford 5-Bromo-4-methoxy-1H-pyrrolo[2,3-b]pyridine (130 mg, 0.57 mmol, 27%) as a light yellow powder. 1H NMR (500 MHz, DMSO-d6) δ 11.84 (bs, 1H), 8.14 (s, 1H), 7.40 (m, 1H), 6.80 (m, 1H), 4.30 (s, 3H). MS: m/z 226.9/228.9 (M+H).

Workup

concentrationThe reaction mixture was concentrated
custompurified by flash silica gel chromatography

Sources & evidence

ORD record: ord-90201bcde7634feb94d23a6163d80c8d
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158647B2

Reaction notes

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