Hydrochloric Acid → HCID 44180965, compound

HRID 1042037Notes

Reaction equation

Br[C:2]1[C:6]2[O:7][C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:9][C:10](=[O:11])[C:5]=2[S:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH:27]([O:29]CCCC)=[CH2:28].Cl>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].CN(C)C=O>[C:27]([C:2]1[C:6]2[O:7][C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:9][C:10](=[O:11])[C:5]=2[S:4][CH:3]=1)(=[O:29])[CH3:28]

Participants

Conditions

Temperature: 180 °C

Procedure

A 2 mL conical microwave vial was charged with a magnetic stirring bar, 3-bromo-5-morpholino-7H-thieno[3,2-b]pyran-7-one (103) (100 mg, 316 gmol), dimethylformamide (0.5 mL), N,N-diisopropylethylamine (165 μL, 949 μmol), butyl vinyl ether (124 μL, 949 gmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (10 mg, 12.6 μmol). The reaction mixture was sealed, and the reaction mixture was magnetically stirred and heated via microwave irradiation to 180° C. for 15 minutes. After cooling to room temperature, the reaction was charged with aqueous hydrochloric acid (1.0 M, 2 mL) and stirred at room temperature for 2 hours to give 3-acetyl-5-morpholino-7H-thieno[3,2-b]pyran-7-one (74).

Workup

additionA 2 mL conical microwave vial was charged with a magnetic stirring bar
customThe reaction mixture was sealed
temperatureAfter cooling to room temperature
stirringstirred at room temperature for 2 hours

Sources & evidence

ORD record: ord-19eb42c5ff284afea1c002af3ab49c71
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557807B2

Reaction notes

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