Cesium carbonate → Methyl 3-hexylquinoline-8-carboxylate

HRID 472791Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][C:11]=2[C:17]([O:19][CH3:20])=[O:18])(=O)=O.[CH2:23](B(O)O)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.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>[CH2:23]([C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][C:11]=2[C:17]([O:19][CH3:20])=[O:18])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

Conditions

Temperature: 95 °C

Procedure

Methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylate (538 mg, 1.6 mmol), hexylboronic acid (415 mg, 3.2 mmol) and Cs2CO3 (779 mg, 2.4 mmol) were suspended in toluene (30 mL). The mixture was purged with nitrogen then tetrakis(triphenylphosphine)palladium (0) (55 mg, 0.05 mmol) was added. The reaction was sealed and heated at 95° C. for 16 h. The mixture was cooled and filtered through celite, rinsing with excess CH2Cl2. The filtrate was concentrated in vacuo. The resulting oil was purified on 40 g silica gel (19:1 CH2Cl2/methyl t-butyl ether) to afford 178 mg (41%) of methyl 3-hexylquinoline-8-carboxylate.

Workup

customThe mixture was purged with nitrogen
customThe reaction was sealed
temperatureThe mixture was cooled
filtrationfiltered through celite
washrinsing with excess CH2Cl2
concentrationThe filtrate was concentrated in vacuo
customThe resulting oil was purified on 40 g silica gel (19:1 CH2Cl2/methyl t-butyl ether)

Sources & evidence

ORD record: ord-c7de980b234a48279a603d7e7bc23c14
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633220B2

Reaction notes

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