Triethylamine → N-(3-ethyl-1-((6-vinylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79320Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][N:14]2[C:22]3[C:17](=[C:18]([NH:23][C:24]([C:26]4[N:30]5[CH:31]=[CH:32][CH:33]=[CH:34][C:29]5=[N:28][CH:27]=4)=[O:25])[CH:19]=[CH:20][CH:21]=3)[C:16]([CH2:35][CH3:36])=[N:15]2)[N:8]=1)(=O)=O.[B-](F)(F)(F)[CH:40]=[CH2:41].[K+].C(N(CC)CC)C>CC(O)C.C1COCC1>[CH2:35]([C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][C:18]=2[NH:23][C:24]([C:26]2[N:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]3=[N:28][CH:27]=2)=[O:25])[N:14]([CH2:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([CH:40]=[CH2:41])[N:8]=2)[N:15]=1)[CH3:36]

Participants

Conditions

Temperature: 80 °C

Procedure

To 6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yl trifluoromethanesulfonate (100 mg, 0.184 mmol) in IPA/THF (3 mL/1 mL) was added potassium trifluoro(vinyl)borate (36.9 mg, 0.275 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (15.0 mg, 0.0184 mmol) and triethylamine (37.2 mg, 0.367 mmol). The reaction mixture was sealed and heated to 80° C. for 16 hours. The mixture was cooled to ambient temperature and concentrated under reduce pressure. The residue was filtered through a plug of silica gel washing with EtOAc. The solution was concentrated to give the product (72 mg).

Workup

customThe reaction mixture was sealed
temperatureThe mixture was cooled to ambient temperature
concentrationconcentrated
filtrationThe residue was filtered through a plug of silica gel washing with EtOAc
concentrationThe solution was concentrated

Sources & evidence

ORD record: ord-ffe0a4f62bba4c418737cb431153b06d
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841455B2

Reaction notes

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