2-(Tributylstannyl)furan → HCID 67366979, compound

HRID 1173067Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C@@H:18]3[CH2:24][C@@H:23]4[C@H:19]3[CH2:20][N:21]([CH2:25][CH2:26][CH3:27])[CH2:22]4)=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:33]1[O:34][CH:35]=[CH:36][CH:37]=1)CCC>O1CCCC1>[CH2:25]([N:21]1[CH2:20][C@@H:19]2[C@@H:23]([CH2:24][C@H:18]2[C:15]2[CH:16]=[CH:17][C:12]([NH:11][S:8]([C:5]3[CH:6]=[CH:7][C:2]([C:33]4[O:34][CH:35]=[CH:36][CH:37]=4)=[CH:3][CH:4]=3)(=[O:10])=[O:9])=[CH:13][CH:14]=2)[CH2:22]1)[CH2:26][CH3:27]

Participants

Conditions

Temperature: 150 °C

Procedure

4-Bromo-N-[4-((1R,5S,6R)-3-propyl-3-aza-bicyclo[3.2.0]hept-6-yl)-phenyl]-benzenesulfonamide (50 mg, 0.11 mmol), 2-(tributylstannyl)-furan (199 mg, 0.56 mmol) and tetrakistriphenylphosphinpalladium(0) (26 mg, 0.02 mmol) were dissolved in 5 ml of tetrahydrofuran and stirred for 40 minutes at 150° C. in the microwave (CEM). The reaction mixture was filtered over celite, washed with methanol, and the filtrate evaporated to dryness under reduced pressure. The residue was purified via silica gel chromatography with ethyl acetate, and ethyl acetate/methanol (15%). Fractions containing the product were combined, the solvent evaporated to yield 4.2 mg of the title product (yield 9%).

Workup

filtrationThe reaction mixture was filtered over celite
washwashed with methanol
customthe filtrate evaporated to dryness under reduced pressure
customThe residue was purified via silica gel chromatography with ethyl acetate, and ethyl acetate/methanol (15%)
additionFractions containing the product
customthe solvent evaporated

Sources & evidence

ORD record: ord-718b104314ad48e1aa7a0970d220f521
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834048B2

Reaction notes

Loading…