Triethylamine → Tert-butyl (1-(2-(7-vinyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

HRID 1041970Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[C:14]([N:21]5[CH2:26][CH2:25][CH:24]([CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:23][CH2:22]5)[CH:15]=[CH:16][CH:17]=4)[N:12]=3)=[N:9][N:10]=[C:4]2[CH:3]=1.[CH2:36](N(CC)CC)[CH3:37]>C1COCC1.CC(O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[CH:36]([C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[C:14]([N:21]5[CH2:22][CH2:23][CH:24]([CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:32])[CH3:33])[CH2:25][CH2:26]5)[CH:15]=[CH:16][CH:17]=4)[N:12]=3)=[N:9][N:10]=[C:4]2[CH:3]=1)=[CH2:37]

Participants

Conditions

Temperature: 60 °C

Procedure

To tert-butyl (1-(2-(7-iodo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate (91 mg, 0.16 mmol) in THF/IPA (2/1 mL) was added C2H3BF3K (31 mg, 0.23 mmol), PdCl2(dppf) dichloromethane adduct (13 mg, 0.016 mmol) and triethylamine (24 mg, 0.23 mmol). The reaction was stirred for 2 hours, followed by heating at 60° C. overnight. The reaction was then cooled to ambient temperature and concentrated, and the residue was purified by flash column chromatography (20:1 Hexane/EtOAc) providing the desired product (90% yield; 0.068 g).

Workup

temperatureThe reaction was then cooled to ambient temperature
concentrationconcentrated
customthe residue was purified by flash column chromatography (20:1 Hexane/EtOAc)

Sources & evidence

ORD record: ord-774d647ec84c4f36a69e6af0f486e676
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557809B2

Reaction notes

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