Ammonia → 5-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxamide

HRID 656019Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11](O)=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:18][CH2:17][S:16](=[O:20])(=[O:19])[CH2:15]1.C1C=CC2N(O)N=[N:27]C=2C=1.N.O1CCOCC1>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:27])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:18][CH2:17][S:16](=[O:20])(=[O:19])[CH2:15]1

Participants

Conditions

Temperature: 100 °C

Procedure

A 20 mL microwave reaction vessel was charged with 5-bromo-3-(1,1-dioxidotetrahydro-3-thienyl)-1H-indole-7-carboxylic acid (0.50 g, 1.40 mmol) EDC (0.81 g, 4.22 mmol), HOBT (0.22 g, 1.40 mmol), and dissolved in DMF (4.65 mL). A 0.5 M solution of ammonia in 1,4 dioxane (5.6 mL, 2.81 mmol) was then added and the reaction was heated in a microwave for 20 minutes, at 100° C. The solution was then dissolved in ethyl acetate and washed with water (3×'s). The aqueous layers were backwashed with ethyl acetate. The organic layers were combined and washed with 6 M sodium hydroxide, brine, dried with magnesium sulfate, and concentrated to give 0.484 g (96%) of the title compound.

Workup

washwashed with water (3×'s)
washwashed with 6 M sodium hydroxide, brine
dry with materialdried with magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-91d5e46b48e84cf09ec5286dc59ada99
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071584B2

Reaction notes

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