Potassium Carbonate → 8-Bromo-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinoline

HRID 1095669Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([Br:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][O:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][N:21]2[CH:24]=[CH:25][N:26]=[C:20]2[CH:19]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].O>[Br:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:24]1[N:21]3[CH:22]=[CH:23][C:18]([O:17][CH2:16][CH2:15][O:14][CH3:13])=[CH:19][C:20]3=[N:26][CH:25]=1)[CH:11]=[CH:10]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2,8-dibromoquinoline (22.4 g, 78.0 mmol), 7-(2-methoxyethoxy)imidazo[1,2-a]pyridine (15.0 g, 78.0 mmol), Pd(PPh3)4 (4.51 g, 3.90 mmol), K2CO3 (21.6 g, 156 mmol) and Pd(OAc)2 (0.876 g, 3.90 mmol), dioxane (312 mL) and water (3 ml) was heated to 100° C. for 18 hours. The resulting mixture was diluted with dichloromethane (500 ml) and filtered. The filtrate was concentrated under reduced pressure and to the resulting oil was added ethyl acetate (100 ml) and methyl tert-butyl ether (100 ml). The resulting mixture was stirred overnight. Filtration to collect the resulting solids yielded the title compound (22.2 g, 72% yield). MS ESI (+) m/z 398 and 400 (M+1 of each isotope) detected.

Workup

filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure and to the resulting oil
additionwas added ethyl acetate (100 ml) and methyl tert-butyl ether (100 ml)
filtrationFiltration
customto collect the resulting solids

Sources & evidence

ORD record: ord-85d9d9830b824c02b2567ddfdce07f9d
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138181B2

Reaction notes

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