Tris(furan-2-yl)phosphane → 2-[4-Methyl-2-(3-pyridyl)thiazol-5-yl]-5,6-dihydrothiopyrano[3,2-d]thiazol-7-one

HRID 2279277Notes

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]1[S:10][C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:8][C:7]=1[CH3:17])CCC.Br[C:27]1[S:28][C:29]2[S:35][CH2:34][CH2:33][C:32](=[O:36])[C:30]=2[N:31]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:17][C:7]1[N:8]=[C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[S:10][C:6]=1[C:27]1[S:28][C:29]2[S:35][CH2:34][CH2:33][C:32](=[O:36])[C:30]=2[N:31]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Tri-n-butyl-[4-methyl-2-(3-pyridyl)thiazol-5-yl]stannane (560 mg, 1.2 mmol, prepared as described previously) and 2-bromo-5,6-dihydrothiopyrano[3,2-d]thiazol-7-one (300 mg, 1.20 mmol), Tris(dibenzylideneacetone)dipalladium(0) (54 mg, 0.06 mmol) and Tri(2-furyl)phosphine (54 mg, 0.23 mmol) were dissolved in 10 ml of dioxane and placed in a steel tube. The mixture were evacuated, flushed with N2 3 times and heated at 100° C. for 18 hours. After cooling to ambient temperature, the mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified with chromatography (Ethyl acetate: Petroleum ether=2/1) to give the title compound (83 mg, 20% yield). 1H NMR (400 Mz, CDCl3): δ2.79 (s, 3H), 3.04 (t, 2H), 3.46 (t, 2H), 7.43-7.45 (m, 1H), 8.43 (d, 1H), 8.69 (d, 1H), 9.20 (s, 1H).

Workup

customplaced in a steel tube
customThe mixture were evacuated
customflushed with N2 3 times
temperatureAfter cooling to ambient temperature
filtrationthe mixture was filtered
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified with chromatography (Ethyl acetate: Petroleum ether=2/1)

Sources & evidence

ORD record: ord-0910eedc1b044301bd5d183c573743b1
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133218B2

Reaction notes

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