Potassium tert-butoxide → 2-(2-tert-butyl-5-chloro-1H-pyrrolo[2,3-c]pyridin-1-yl)ethanol

HRID 1044022Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][OH:11])=[C:4]([C:12]#[C:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1.CC([O-])(C)C.[K+]>CN(C=O)C>[C:14]([C:13]1[N:8]([CH2:9][CH2:10][OH:11])[C:5]2=[CH:6][N:7]=[C:2]([Cl:1])[CH:3]=[C:4]2[CH:12]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-(6-chloro-4-(3,3-dimethylbut-1-ynyl)pyridin-3-ylamino)ethanol (3.6 g, 14.3 mmol) in DMF (100 mL) was added t-BuOK (3.1 g, 28 mol) under N2 atmosphere. The mixture was heated at 80° C. for 12 h and then was quenched with H2O (200 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (150 mL×3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and purified by chromatography on silica gel (3% ethyl acetate in petroleum ether as eluant) to afford 2-(2-tert-butyl-5-chloro-1H-pyrrolo[2,3-c]pyridin-1-yl)ethanol (1.6 g, 44%). 1H-NMR (CDCl3, 300 MHz) δ 8.50 (s, 1H), 7.39 (s, 1H), 6.28 (s, 1H), 4.55 (t, J=6.6, 2H), 4.05 (t, J=6.6, 2H), 1.49 (s, 9H).

Workup

customwas quenched with H2O (200 mL)
customThe organic layer was separated
extractionthe aqueous layer was extracted with EtOAc (150 mL×3)
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous Na2SO4
custompurified by chromatography on silica gel (3% ethyl acetate in petroleum ether as eluant)

Sources & evidence

ORD record: ord-986d70a82b9b45f29f6dae22ab1ba7df
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563573B2

Reaction notes

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