Ammonia → 5-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide

HRID 656012Notes

Reaction equation

N.O1CCOCC1.[Br:8][C:9]1[CH:10]=[C:11]2[C:15](=[C:16]([C:18](O)=[O:19])[CH:17]=1)[NH:14][CH:13]=[C:12]2[CH:21]1[CH2:26][CH2:25][S:24](=[O:28])(=[O:27])[CH2:23][CH2:22]1.C1C=CC2N(O)N=[N:35]C=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O.CCOC(C)=O>[Br:8][C:9]1[CH:10]=[C:11]2[C:15](=[C:16]([C:18]([NH2:35])=[O:19])[CH:17]=1)[NH:14][CH:13]=[C:12]2[CH:21]1[CH2:26][CH2:25][S:24](=[O:28])(=[O:27])[CH2:23][CH2:22]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 0.5 M NH3 in dioxane (12 mL, 6 mmol) was added to a mixture of 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylic acid (1.1 g, 2.96 mmol), HOBt (0.455 g, 2.96 mmol), and EDC.HCl (1.54 g, 8.02 mmol) in DMF (4 mL) in a Biotage microwave vial. The vial was sealed, and the reaction was heated at 100° C. for 20 min on regular absorbance in a Biotage Initiator microwave. EtOAc (75 mL) and H2O (75 mL) were added, the layers were separated, and the aqueous layer was extracted with EtOAc (4×100 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to give a light yellow solid. The solid was washed with DCM (1×25 mL) to and aspirated dry to give 2.05 g (96%) of the title compound.

Workup

customThe vial was sealed
customthe layers were separated
extractionthe aqueous layer was extracted with EtOAc (4×100 mL)
dry with materialThe combined organic layers were dried (Na2SO4)
concentrationconcentrated under reduced pressure
customto give a light yellow solid
washThe solid was washed with DCM (1×25 mL) to and
customaspirated dry

Sources & evidence

ORD record: ord-bb53a576b1d44c1cafd59f9178226e13
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071584B2

Reaction notes

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