Triethylamine → 8-(Tert-butyldimethylsilyloxy)-2-(7-vinyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline

HRID 2035557Notes

Reaction equation

[Si:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([C:19]1[N:23]3[CH:24]=[CH:25][C:26](I)=[CH:27][C:22]3=[N:21][N:20]=1)[CH:15]=[CH:14]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:29]([Sn](CCCC)(CCCC)C=C)[CH2:30]CC.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.C(N(CC)CC)C>CN1C(=O)CCC1.C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([C:19]1[N:23]3[CH:24]=[CH:25][C:26]([CH:29]=[CH2:30])=[CH:27][C:22]3=[N:21][N:20]=1)[CH:15]=[CH:14]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To 8-(tert-butyldimethylsilyloxy)-2-(7-iodo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline (2.011 g, 4.003 mmol) in NMP/THF (10 mL/10 mL) was added tributyl(vinyl)stannane (1.523 g, 4.803 mmol), trifuran-2-ylphosphine (0.0929 g, 0.400 mmol), Pd2 dba3 (0.367 g, 0.4003 mmol) and triethylamine (0.405 g, 4.00 mmol). The reaction was degassed with N2 and heated to 60° C. for 1 hour. The crude mixture was diluted with ethyl acetate and the organic layer was washed with H2O. The combined organics fractions were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash column chromatography (eluting with a 5:1 mixture of Hexanes/ethyl acetate), affording the desired product.

Workup

customThe reaction was degassed with N2
additionThe crude mixture was diluted with ethyl acetate
washthe organic layer was washed with H2O
dry with materialThe combined organics fractions were dried over Na2SO4
concentrationconcentrated in vacuo
customThe crude material was purified by flash column chromatography (
washeluting with a 5:1 mixture of Hexanes/ethyl acetate),

Sources & evidence

ORD record: ord-5a698644e63746de8afba0934a6ba03a
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575145B2

Reaction notes

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