Acetic Acid → HCID 86651943, compound

HRID 447516Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]2[C:17]3[C:12](=[CH:13][C:14]([C:18]#N)=[CH:15][CH:16]=3)[NH:11][N:10]=2)=[CH:3][CH:2]=1.N1C=CC=CC=1.C(O)(=[O:28])C>CN(C=O)C.O.[Ni]>[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]2[C:17]3[C:12](=[CH:13][C:14]([CH:18]=[O:28])=[CH:15][CH:16]=3)[NH:11][N:10]=2)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

The crude (E)-3-(2-(pyridin-4-yl)vinyl)-1H-indazole-6-carbonitrile was dissolved in DMF (10 mL). Pyridine (10 mL) and acetic acid (5 mL) were added, followed by NaH2PO2/H2O (1.76 g, 20 mmol/5 mL) and Raney-Nickel 2400 (slurry in H2O, 1 mL). The resulting mixture was heated at 60° C. for 1 h before cooling to rt. The mixture was diluted with H2O and extracted with EtOAc (50 mL×3). The combined extracts were dried (Na2SO4) and concentrated to give an orange liquid. H2O (50 mL) was added and the resulting suspension was sonicated, suction filtered, rinsed with H2O and dried to give crude (E)-3-(2-(pyridin-4-yl)vinyl)-1H-indazole-6-carbaldehyde (540 mg) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ 13.90 (s, 1H), 10.15 (s, 1H), 8.57 (d, 2H, J=4.0 Hz), 8.40 (d, 1H, J=8.0 Hz), 8.20 (s, 1H), 7.89 (d, 1H, J=16.4 Hz), 7.73-7.68 (m, 3H), 7.55 (d, 1H, J=16.8 Hz); MS ESI 249.9 [M+H]+, calcd for [C23H16N4O+H]+ 250.1.

Workup

temperaturebefore cooling to rt
extractionextracted with EtOAc (50 mL×3)
dry with materialThe combined extracts were dried (Na2SO4)
concentrationconcentrated
customto give an orange liquid
customthe resulting suspension was sonicated
filtrationsuction filtered
washrinsed with H2O
customdried

Sources & evidence

ORD record: ord-0b0cd7bd60fa476aad264cd1261989e2
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481525B2

Reaction notes

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