Cesium carbonate → methyl 3-hydroxy-4-(5-morpholino-7-oxo-7H-thieno[3,2-b]pyran-3-yl)thiophene-2-carboxylate

HRID 1042028Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[O:12][C:11]3[C:13](B(O)O)=[CH:14][S:15][C:10]=3[C:9](=[O:19])[CH:8]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:27]1[C:28]([OH:36])=[C:29]([C:32]([O:34][CH3:35])=[O:33])[S:30][CH:31]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(COC)OC>[OH:36][C:28]1[C:27]([C:13]2[C:11]3[O:12][C:7]([N:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)=[CH:8][C:9](=[O:19])[C:10]=3[S:15][CH:14]=2)=[CH:31][S:30][C:29]=1[C:32]([O:34][CH3:35])=[O:33]

Participants

Conditions

Temperature: 140 °C

Procedure

A 2 mL conical microwave vial was charged with a magnetic stirring bar, 5-morpholino-7-oxo-7H-thieno[3,2-b]pyran-3-ylboronic acid (69) (57 mg, 0.16 mmol), cesium carbonate (102 mg, 0.31 mmol), methyl 4-bromo-3-hydroxythiophene-2-carboxylate (56 mg, 0.24 mmol), tetrakis(triphenylphosphine)palladium(0) (9 mg, 0.08 mmol), and dimethoxyethane (0.5 mL). The reaction mixture was magnetically stirred and heated via microwave irradiation for 15 minutes at 140° C. Upon cooling to room temperature, the reaction was concentrated in vacuo and purified using high-pressure liquid chromatography to give methyl 3-hydroxy-4-(5-morpholino-7-oxo-7H-thieno[3,2-b]pyran-3-yl)thiophene-2-carboxylate (21).

Workup

additionA 2 mL conical microwave vial was charged with a magnetic stirring bar
temperatureUpon cooling to room temperature
concentrationthe reaction was concentrated in vacuo
custompurified

Sources & evidence

ORD record: ord-1daffc2910d340f8943cc3b9325e89a9
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557807B2

Reaction notes

Loading…