Cesium carbonate → HCID 44180968, compound

HRID 1042041Notes

Reaction equation

I[C:2]1[CH:18]=[CH:17][C:5]([C:6]([O:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:7])=[CH:4][CH:3]=1.Br[C:20]1[C:24]2[O:25][C:26]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[CH:27][C:28](=[O:29])[C:23]=2[S:22][CH:21]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>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].COCCOC>[O:33]1[CH2:34][CH2:35][N:30]([C:26]2[O:25][C:24]3[C:20]([C:2]4[CH:18]=[CH:17][C:5]([C:6]([O:8][CH2:9][CH2:10][N:11]5[CH2:16][CH2:15][O:14][CH2:13][CH2:12]5)=[O:7])=[CH:4][CH:3]=4)=[CH:21][S:22][C:23]=3[C:28](=[O:29])[CH:27]=2)[CH2:31][CH2:32]1

Participants

Conditions

Temperature: 140 °C

Procedure

A 2 mL microwave vial was charged with a magnetic stirring bar, 2-morpholinoethyl 4-iodobenzoate (90 mg, 249 μmol), 3-bromo-5-morpholino-7H-thieno[3,2-b]pyran-7-one (103) (79 mg, 249 μmol), bis(pinacolato)diboron (70 mg, 274 gmol), cesium carbonate (325 mg, 997 dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (6 mg, 7 μmol), and 1,2-dimethoxyethane (1 mL). The reaction mixture was sealed, and the reaction mixture was magnetically stirred and heated under microwave irradiation to 140° C. for 15 minutes to give 2-morpholinoethyl 4-(5-morpholino-7-oxo-7H-thieno[3,2-b]pyran-3-yl)benzoate (77).

Workup

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

Sources & evidence

ORD record: ord-59e1b641745047f5ad18fa76b763278d
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557807B2

Reaction notes

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