4-Vinylpyridine → HCID 86651955, compound

HRID 1615269Notes

Reaction equation

N1C=CC([C:7]2[CH:15]=[C:14]([CH:16]=[O:17])[CH:13]=[C:12]3[C:8]=2[CH:9]=[N:10][N:11]3[CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=CC=1.[N:26]1[CH:31]=[CH:30][C:29]([CH:32]=[CH2:33])=[CH:28][CH:27]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CCN(C(C)C)C(C)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[N:26]1[CH:31]=[CH:30][C:29](/[CH:32]=[CH:33]/[C:7]2[CH:15]=[C:14]([CH:16]=[O:17])[CH:13]=[C:12]3[C:8]=2[CH:9]=[N:10][N:11]3[CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:23])[CH3:24])=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 4-(pyridine-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (50 mg, 0.14 mmol) and 4-pyridylethylene (20 μL, 0.19 mmol) in acetonitrile (1.5 mL) was purged with argon. Palladium acetate (2 mg, 0.007 mmol), tri-o-tolylphosphine (4 mg, 0.014 mmol) and DIPEA (50 μL) was added and the mixture was heated to 70° C. for 16 h. Ethyl acetate (50 mL) was added and the mixture was washed with water (2×5 mL), brine (5 mL), dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography (98:2 EtOAc/MeOH) to give the title compound as a yellow solid (28 mg, 53%). MS ESI [M+H]+, calcd for [C21H25N3O2Si+H]+ 380.2; found m/z 380.2.

Workup

washthe mixture was washed with water (2×5 mL), brine (5 mL)
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by silica gel chromatography (98:2 EtOAc/MeOH)

Sources & evidence

ORD record: ord-e52791afbec743feb9bff1b942b20953
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765748B2

Reaction notes

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