1,4-Dioxane → HCID 89751832, compound

HRID 1521798Notes

Reaction equation

Br[C:2]1[S:3][C:4]2[CH2:14][CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10](Br)[CH:11]=3)[C:5]=2[N:6]=1.C([Sn](CCCC)(CCCC)C([O:23][CH2:24][CH3:25])=C)CCC.[F-].[K+].[O:36]1CCO[CH2:38][CH2:37]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:6]1[C:5]2[C:7]3[C:12]([CH2:13][CH2:14][C:4]=2[S:3][C:2]=1[C:24](=[O:23])[CH3:25])=[CH:11][C:10]([C:37](=[O:36])[CH3:38])=[CH:9][CH:8]=3

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 2,7-dibromo-4,5-dihydronaphtho[1,2-d]thiazole (4b) (1.7 g, 5.07 mmol) in 30 ml of anhydrous dioxane was degassed by passing nitrogen gas for 15 min. Tributyl(1-ethoxyvinyl)stannane (4.58 g, 12.68 mmol) was added to it followed by PdCl2(PPh3)2 (0.36 g, 0.51 mmol) and the solution was heated at 90° C. overnight. After cooling, the volume of dioxane was reduced and a saturated solution of KF was added to it and stirred for 15 min., after which the mixture was passed through a pad of celite and washed with ethyl acetate. The combined filtrate was stirred with 4 N HCl solution for 1 h and the organic layer was dried and concentrated and the residue was purified by column chromatography to obtain the diacetyl compound (4c) (1.37 g, 73%). m/z 271.0 (M+).

Workup

customfor 15 min
temperatureAfter cooling
washwashed with ethyl acetate
stirringThe combined filtrate was stirred with 4 N HCl solution for 1 h
customthe organic layer was dried
concentrationconcentrated
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-d3bb892cf8c24658a6a2bb75a19d1d65
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073942B2

Reaction notes

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