Tributylvinyltin → HCID 89444291, compound

HRID 593208Notes

Reaction equation

Br[C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:16])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[N:6][CH:7]=1.[CH2:17]([Sn](CCCC)(CCCC)C=C)[CH2:18]CC.[Cl-].[Li+]>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>[O:16]=[C:9]([NH:8][C:5]1[CH:4]=[N:3][C:2]([CH:17]=[CH2:18])=[CH:7][N:6]=1)[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

Conditions

Temperature: 150 °C

Procedure

Methyl 4-[(5-bromopyrazin-2-yl)amino]-4-oxo-butanoate (A2, 1.00 g, 3.47 mmol) was dissolved in toluene in a microwave vial and tributyl vinyl tin (1.22 g, 3.82 mmol), lithium chloride (0.178 g, 4.17 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.405 g, 0.347 mmol) were added. Argon was bubbling through the mixture for ca. 5 min and the vial was heated under microwave irradiation for 5 min at 150° C. The mixture was diluted with ethyl acetate, washed with water and brine, dried and evaporated. The product was purified by flash chromatography (AcOEt/cyclohexane: 1/99→99/1) to give methyl 4-oxo-4-[(5-vinylpyrazin-2-yl)amino]butanoate A32 (0.42 g, 1.8 mmol, 51% Yield). 1H NMR (400 MHz, CDCl3) 9.42 (1H, s), 9.15 (1H, s), 8.22 (1H, s), 6.72 (1H, m), 6.21 (1H, d), 5.48 (1H, s), 3.72 (3H, s), 2.78 (4H, m).

Workup

additionwere added
customArgon was bubbling through the mixture for ca. 5 min
additionThe mixture was diluted with ethyl acetate
washwashed with water and brine
customdried
customevaporated
customThe product was purified by flash chromatography (AcOEt/cyclohexane: 1/99→99/1)

Sources & evidence

ORD record: ord-f774b9ce56ee4b65969b841363074144
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09241489B2

Reaction notes

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