Tetrahydrofuran → 5-[6-(1-{[tert-Butyl(dimethyl)silyl]oxy}-1-methylethyl)pyridin-3-yl]-2-nitrothiophene-3-carboxamide

HRID 385735Notes

Reaction equation

Br[C:2]1[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([C:10]([NH2:12])=[O:11])[CH:3]=1.[Si:13]([O:20][C:21]([C:24]1[CH:29]=[CH:28][C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][N:25]=1)([CH3:23])[CH3:22])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C1COCC1.C([O-])([O-])=O.[Na+].[Na+]>O.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>[Si:13]([O:20][C:21]([C:24]1[N:25]=[CH:26][C:27]([C:2]2[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([C:10]([NH2:12])=[O:11])[CH:3]=2)=[CH:28][CH:29]=1)([CH3:23])[CH3:22])([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 90 °C

Procedure

5-Bromo-2-nitrothiophene-3-carboxamide (602 mg, 2.40 mmol), 2-(1-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (905 mg, 2.40 mmol), and Pd(PPh3)4 (139 mg, 0.12 mmol) were combined in a vial and evacuated/backfilled with nitrogen. THF (5.6 mL) and 2 N Na2CO3 (2.4 mL) were added, and the reaction was stirred at 90° C. overnight. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Flash chromatography of the crude residue (10-100% EtOAc/hexanes) afforded the title compound as a yellow solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with EtOAc (2×)
washThe combined organic layers were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-224a4c1f6eba460eabcf1c99d17ea4ad
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367706B2

Reaction notes

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