Ethanol → HCID 11849758, compound

HRID 1930494Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[CH3:16]CO.[O:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>O>[CH:12]([C:11]1[CH:14]=[CH:15][C:8]([C:5]2[N:6]=[CH:7][C:2]([C:23]3[O:22][C:21]([CH:20]=[O:19])=[CH:16][CH:24]=3)=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)=[O:13]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 6 (10 mmol) in 40 mL dry 1,4-dioxane was added palladium tetrakis-triphenylphosphine (400 mg), then 5-(diethoxymethyl-furan-2-yl)-trimethylstannane (10 mmol) was added and the reaction mixture was refluxed at 100° C. for 24 h. The solvent was then evaporated to dryness to give a dark brown residue that was suspended in water and extracted with CH2Cl2. The organic layer was passed over hyflo, dried (Na2SO4) and evaporated to dryness under reduced pressure, followed by acid hydrolysis with 2M HCl to furnish 7. Yield 79%; mp 204-206° C. (EtOH). 1H NMR (DMSO-d6); δ 7.55 (d, J=3.6 Hz, 1H), 7.73 (d, J=3.6 Hz, 1H), 8.06 (d, J=8.4 Hz, 2H), 8.27 (d, J=8.4 Hz, 1H), 8.37-8.41 (m, 3H), 9.24 (d, J=2.1 Hz, 1H), 9.67 (s, 1H), 10.09 (s, 1H). 13C NMR (DMSO-d6); δ 192.8, 178.1, 155.2, 154.7, 152.3, 146.3, 142.9, 136.5, 133.3, 130.0, 127.2, 125.1, 124.3, 121.4, 110.6. Anal. Calc. for C17H11NO3: C %, 73.63; H %, 3.99. Found C %, 73.75; H %, 3.81.

Workup

customThe solvent was then evaporated to dryness
customto give a dark brown residue that
extractionextracted with CH2Cl2
dry with materialdried (Na2SO4)
customevaporated to dryness under reduced pressure
customfollowed by acid hydrolysis with 2M HCl
customto furnish 7

Sources & evidence

ORD record: ord-dd16e7afd188470e83b10793dfb60169
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188121B2

Reaction notes

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