Diisopropylamine → 3-Bromo-6-methoxy-2-(3-methyl-1-butyn-1-yl)pyridine

HRID 2357931Notes

Reaction equation

C(N[CH:5]([CH3:7])[CH3:6])(C)C.Br[C:9]1[C:14]([Br:15])=[CH:13][CH:12]=[C:11]([O:16][CH3:17])[N:10]=1.[CH2:18]1COC[CH2:19]1>[Cu](I)I>[Br:15][C:14]1[C:9]([C:18]#[C:19][CH:5]([CH3:6])[CH3:7])=[N:10][C:11]([O:16][CH3:17])=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 70 °C

Procedure

In a nitrogen atmosphere, tetrakis-triphenylphosphine palladium (5.15 g), copper iodide (5.95 g), diisopropylamine (15 mL) and 3-methyl-2-butyne (38.1 g) were added to the compound of Example 260 (131 g) in THF (150 mL). The mixture was placed in a sealed vessel and stirred at 70° C. for 21 hours. The resulting salt was removed by filtration and the filtrate was mixed with silica gel for condensation. The silica gel was directly eluted (ether:petroleumether=5:95) and the collected eluate was distilled (93° C., 0.1 mmHg) to afford the title compound as a pale yellow oil (121 g).

Workup

customThe mixture was placed in a sealed vessel
customThe resulting salt was removed by filtration
additionthe filtrate was mixed with silica gel for condensation
washThe silica gel was directly eluted (ether:petroleumether=5:95)
distillationthe collected eluate was distilled (93° C., 0.1 mmHg)

Sources & evidence

ORD record: ord-90b91307c454402887670103d2c57395
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763617B2

Reaction notes

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