HCID 21877256, compound → HCID 135839319, compound

HRID 1862099Notes

Reaction equation

C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:23]=[C:22]3[C:18]([C:19]([C:24]4[CH:33]=[CH:32][C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[CH:25]=4)=[N:20][NH:21]3)=[CH:17][CH:16]=2)=[CH:11][C:10]=1[O:34][CH3:35])C1C=CC=CC=1>C(OCC)(=O)C.C1C=CC=CC=1.CO.[Pd]>[CH:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:32]=[CH:33][C:24]=1[C:19]1[C:18]2[C:22](=[CH:23][C:15]([C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([O:34][CH3:35])[CH:11]=3)=[CH:16][CH:17]=2)[NH:21][N:20]=1

Participants

Conditions

Temperature: 23 °C

Procedure

6-(4-Benzyloxy-3-methoxy-phenyl)-3-naphthalen-2-yl-1H-indazole (25 mg, 0.055 mmol) was dissolved in a mixture of ethyl acetate (2 mL), benzene (2 mL) and methanol (2 mL). To this solution was added palladium on carbon (25 mg, 10% wt) and the reaction vessel was vacuum/purged with hydrogen gas for five cycles. The reaction mixture was allowed to stir for 3 days (d) at 23° C. and was filtered through a plug of Celite. Concentration and purification by silica gel chromatography afforded 3-(Naphthalen-2-yl)-6-(3-methoxy-4-hydroxy-phenyl)-1H-indazole (8 mg, 40%): 1H NMR (CDCl3) δ 10.3 (bs, 1H), 8.50 (s, 1H), 8.20 (d, 1H, J=8 Hz), 7.98 (d, 1H, J=8Hz), 7.90 (m, 1H), 7.7-6.8 (m, 9H), 3.98 (s, 3H). MS (ES) [m+H]/z Calc'd 367, found 367, [m−H]/z Calc'd 365, found 365.

Workup

customthe reaction vessel was vacuum/purged with hydrogen gas for five cycles
filtrationwas filtered through a plug of Celite
concentrationConcentration and purification by silica gel chromatography

Sources & evidence

ORD record: ord-6f0d289e5307480081f046fd7ce3456e
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06534524B1

Reaction notes

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