Dibutylamine → HCID 63961710, compound

HRID 529035Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2,6-dibromopyridine (Aldrich, 1.42 g, 6.00 mmol) in DMF (2.0 mL) were added dibutylamine (Aldrich, 388 g, 3.00 mmol) and potassium carbonate (829 mg, 6.00 mmol). The reaction mixture was heated at 90° C. for 20 h. After cooling to room temperature, the reaction mixture was quenched by adding cold water. The mixture was extracted with DCM (3×), and the combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to give a crude oil. Purification using flash column chromatography (eluting with DCM) provided the title compound (368 mg, 43%) as a light brown oil. 1H NMR (CDCl3) δ 0.22 (dd, J=8.4, 7.4 Hz, 1H), 6.62 (d, J=7.0 Hz, 1H), 6.33 (d, J=8.3 Hz, 1H), 3.49-3.37 (m, 4H), 1.65-1.52 (m, 4H), 1.44-1.30 (m, 4H), 0.98 (t, J=7.3 Hz, 6H); MS(ESI+) m/z 272.1 (M+H)+.

Workup

temperatureAfter cooling to room temperature
customthe reaction mixture was quenched
additionby adding cold water
extractionThe mixture was extracted with DCM (3×)
dry with materialthe combined organic extracts were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a crude oil
customPurification
washflash column chromatography (eluting with DCM)

Sources & evidence

ORD record: ord-f2a98e8c7bb84920bbacb7b469136e82
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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