Morpholine → HCID 44180963, compound

HRID 1042035Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[O:13][C:14]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:15][C:16](=[O:17])[C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[NH:64]1[CH2:69][CH2:68][O:67][CH2:66][CH2:65]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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(COC)OC>[O:21]1[CH2:22][CH2:23][N:18]([C:14]2[O:13][C:12]3[C:8]([C:5]4[CH:6]=[CH:7][C:2]([N:64]5[CH2:69][CH2:68][O:67][CH2:66][CH2:65]5)=[CH:3][CH:4]=4)=[CH:9][S:10][C:11]=3[C:16](=[O:17])[CH:15]=2)[CH2:19][CH2:20]1

Participants

Conditions

Temperature: 150 °C

Procedure

A 2 mL conical microwave vial was charged with a magnetic stirring bar, 3-(4-chlorophenyl)-5-morpholino-7H-thieno[3,2-b]pyran-7-one (17) (80 mg, 230 μmol), sodium tert-butoxide (31 mg, 322 μmol), tris(dibenzylideneacetone)dipalladium(0) (3 mg, 3.5 μmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (8.8 mg, 21 μmol), dimethoxyethane (0.5 mL), and morpholine (24 μL, 276 μmol). The reaction mixture was sealed, and the reaction mixture was magnetically stirred and heated via microwave irradiation to 150° C. for 15 minutes to give 5-morpholino-3-(4-morpholinophenyl)-7H-thieno[3,2-b]pyran-7-one (72).

Workup

additionA 2 mL conical microwave vial was charged with a magnetic stirring bar
customThe reaction mixture was sealed

Sources & evidence

ORD record: ord-98cb7bd5d91f4fc49d2f3fdfe4f141f7
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557807B2

Reaction notes

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