Water → N-(2-(5-bromo-7-chlorobenzofuran-2-yl)ethyl)-2,2-dimethoxyethanamine

HRID 2179427Notes

Reaction equation

CC1C=CC(S(O[CH2:12][CH2:13][C:14]2[O:15][C:16]3[C:22]([Cl:23])=[CH:21][C:20]([Br:24])=[CH:19][C:17]=3[CH:18]=2)(=O)=O)=CC=1.[CH3:25][O:26][CH:27]([O:30][CH3:31])[CH2:28][NH2:29].O>O1CCOCC1>[Br:24][C:20]1[CH:21]=[C:22]([Cl:23])[C:16]2[O:15][C:14]([CH2:13][CH2:12][NH:29][CH2:28][CH:27]([O:30][CH3:31])[O:26][CH3:25])=[CH:18][C:17]=2[CH:19]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of the product of Example 84, step C (2.0 g, 4.65 mmol) in dioxane (10 mL) was added 2,2-dimethoxyethanamine (1.47 g, 13.95 mmol). The reaction mixture was heated to 90° C. for 3 h, cooled to ambient temperature, treated with water (20 mL) and extracted with dichloromethane (3×20 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and the filtrate concentrated in vacuo. Purification by flash column chromatography (SiO2, hexanes/ethyl acetate) gave N-(2-(5-bromo-7-chlorobenzofuran-2-yl)ethyl)-2,2-dimethoxyethanamine (1.27 g, 75%) as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 7.49 (d, J=1.8 Hz, 1H), 7.33 (d, J=1.8 Hz, 1H), 6.44 (s, 1H), 4.48 (t, J=5.5 Hz, 2H), 3.38 (s, 6H), 3.09-2.94 (m, 4H), 2.78 (d, J=5.4 Hz, 2H).

Workup

temperaturecooled to ambient temperature
extractionextracted with dichloromethane (3×20 mL)
washThe combined organic extracts were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationthe filtrate concentrated in vacuo
customPurification by flash column chromatography (SiO2, hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-c89270f75ca34a0986bcaa421d8aecc1
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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