Hydrochloric Acid → HCID 89785125, compound

HRID 1056049Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:8]([C:17]([F:20])([F:19])[F:18])=[N:7]2.C([Sn](CCCC)(CCCC)[C:26]([O:28]CC)=[CH2:27])CCC.Cl>C1(C)C=CC=CC=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:13]([NH:12][C:9]1[C:8]([C:17]([F:20])([F:19])[F:18])=[N:7][C:6]2[C:11]([N:10]=1)=[C:2]([C:26](=[O:28])[CH3:27])[CH:3]=[CH:4][CH:5]=2)([CH3:16])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 8-bromo-N-(tert-butyl)-3-(trifluoromethyl)quinoxalin-2-amine (206 mg, 0.592 mmol), tributyl(1-ethoxyvinyl)stannane (300 μl, 0.888 mmol; Aldrich), and Pd(PPh3)4 (0) (68.4 mg, 0.059 mmol) in toluene (5.9 ml) was heated to 100° C. for 8 h; more Pd(PPh3)4 (0) (68.4 mg, 0.059 mmol) and tributyl(1-ethoxyvinyl)stannane (300 μl, 0.888 mmol) were added and the reaction was stirred at 100° C. for another 16 h. Concentrated HCl (61.6 μl, 0.740 mmol) was then added, and the resulting mixture was concentrated onto silica gel. Chromatographic purification (silica gel, 100% hexanes to 10% EtOAc in hexanes) provided 1-(3-(tert-butylamino)-2-(trifluoromethyl)quinoxalin-5-yl)ethanone (224e, >99% yield) as a light yellow solid. MS (ESI, pos. ion) m/z: 312.2 (M+1).

Workup

concentrationthe resulting mixture was concentrated onto silica gel
customChromatographic purification (silica gel, 100% hexanes to 10% EtOAc in hexanes)

Sources & evidence

ORD record: ord-6b052529ce264d6884e4a5a7e81e6d90
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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