Ammonia → 2-(5-amino-2-tert-butyl-1H-pyrrolo[2,3-c]pyridin-1-yl)ethanol

HRID 513091Notes

Reaction equation

[C:1]([C:5]1[N:14]([CH2:15][CH2:16][OH:17])[C:8]2=[CH:9][N:10]=[C:11](Cl)[CH:12]=[C:7]2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH3:18]>CO>[NH2:18][C:11]1[CH:12]=[C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[N:14]([CH2:15][CH2:16][OH:17])[C:8]2=[CH:9][N:10]=1

Participants

Conditions

Temperature: 120 °C

Procedure

In a 100 mL autoclave, a mixture of 2-(2-tert-butyl-5-chloro-1H-pyrrolo[2,3-c]pyridin-1-yl)ethanol (350 mg, 1.39 mmol) and CuSO4.5H2O (35 mg, 1.4 mmol) in aqueous ammonia (14 mL) and CH3OH (7 ml) was heated to 120° C. for 14 h. The mixture was allowed to cool down to 25° C. The methanol was removed by evaporation under vacuum and the resulting mixture was extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and purified by chromatography on silica gel (5% CH3OH in dichloromethane as eluant) to afford 2-(5-amino-2-tert-butyl-1H-pyrrolo[2,3-c]pyridin-1-yl)ethanol (50 mg, 16%). 1H-NMR (CDCl3, 300 MHz) δ 8.22 (s, 1H), 6.59 (s, 1H), 6.08 (s, 1H), 4.44 (t, J=6.9 Hz, 2H), 3.99 (t, J=6.9 Hz, 2H), 1.45 (s, 9H).

Workup

temperatureto cool down to 25° C
customThe methanol was removed by evaporation under vacuum
extractionthe resulting mixture was extracted with ethyl acetate (50 mL×3)
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous Na2SO4
custompurified by chromatography on silica gel (5% CH3OH in dichloromethane as eluant)

Sources & evidence

ORD record: ord-9de53b9047b34a1d818420cbf950ef72
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102672B2

Reaction notes

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