1-Bromonaphthalene → HCID 21106086, compound

HRID 1354570Notes

Reaction equation

[CH2:1]([S:3][C:4]1[N:8]2[C:9]([Sn](CCCC)(CCCC)CCCC)=[CH:10][CH:11]=[CH:12][C:7]2=[CH:6][N:5]=1)[CH3:2].Br[C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[F-].[Cs+]>O1CCOCC1.C(OCC)C>[CH2:1]([S:3][C:4]1[N:8]2[C:9]([C:35]3[C:36]4[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:32]=[CH:33][CH:34]=3)=[CH:10][CH:11]=[CH:12][C:7]2=[CH:6][N:5]=1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of the title C compound, 3-ethylsulfanyl-5-tributylstannyl-imidazo-[1,5-a]pyridine (550 mg, 1.18 mmol) in 1,4-dioxane (8 mL), 1-bromonaphthalene (0.18 mL, 1.29 mmol) is added followed by tris(dibenzylidineacetone)dipalladium(0) (38 mg, 0.041 mmol), tri-t-butylphosphine (80 μL, 0.329 mmol) and cesium fluoride (396 mg, 2.6 mmol). The suspension is heated at 100° C. under nitrogen in a sealed tube for two days. The mixture is cooled, diluted with ethyl ether and filtered through a short silica plug. The solvent is evaporated under reduced pressure, and the residue is purified by flash column chromatography on silica using 10% ethyl acetate in hexanes to yield 3-ethylsulfanyl-5-naphthalen-1-yl-imidazo[1,5-a]pyridine as an amber oil: 1H-NMR (CDCl3) δ 8.01 (dd, J=7.5, 1.8, 1H), 7.93 (d, J=8.1, 1H), 7.61 (s, 1H), 7.58–7.47 (m, 4H), 7.41–7.32 (m, 2H), 6.78 (dd, J=9.0, 6.6, 1H), 6.51 (dd, J=6.6, 1.2, 1H), 2.66 (q, J=7.2, 2H), 0.86 (t, J=7.2, 3H); MS (M+1)+ 305.

Workup

temperatureThe mixture is cooled
filtrationfiltered through a short silica plug
customThe solvent is evaporated under reduced pressure
customthe residue is purified by flash column chromatography on silica using 10% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-7ace2ec3ad5343cf89b12b6d7b94923f
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223866B2

Reaction notes

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