4-(benzyloxy)-1-ethyl-6-fluoro-3-(2-(isoindolin-2-yl)ethyl)-1H-indole → 1-ethyl-6-fluoro-3-(2-(isoindolin-2-yl)ethyl)-1H-indol-4-ol
Reaction equation
C([O:8][C:9]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]2[C:10]=1[C:11]([CH2:21][CH2:22][N:23]1[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:24]1)=[CH:12][N:13]2[CH2:19][CH3:20])C1C=CC=CC=1>CO.[Pd]>[CH2:19]([N:13]1[C:14]2[CH:15]=[C:16]([F:18])[CH:17]=[C:9]([OH:8])[C:10]=2[C:11]([CH2:21][CH2:22][N:23]2[CH2:24][C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:31]2)=[CH:12]1)[CH3:20]Participants
4
Procedure
To a solution of 31-3 (30 mg, 0.072 mmol) in methanol (10 mL) was added 10% Pd/C (20 mg) under hydrogen atmosphere. The reaction mixture was stirred at room temperature overnight and then filtered through a pad of celite. The filtrate was concentrated to give a pale yellow residue, which was purified on silica gel column chromatography eluting with dichloromethane/methanol (9:1) to give 31-4 (25 mg, 70%) as a white solid. 1H-NMR (400 MHz, CDCl3): δ (ppm) 7.29 (d, J=2.4 Hz, 2H), 7.17 (d, J=3.2 Hz, 2H), 6.76 (s, 1H), 6.50 (d, J=8.8 Hz, 1H), 6.30 (d, J=10.8 Hz, 1H), 5.00-4.96 (br.s, 2H), 4.34-4.32 (br.s, 2H), 3.96 (q, 2H), 3.59-3.57 (br.s, 2H), 3.32-3.30 (br.s, 2H), 1.37 (t, J=7.6 Hz, 3H). LRMS: calc 324.2 and found: 325.1 [M+1].
Workup
- filtrationfiltered through a pad of celite
- concentrationThe filtrate was concentrated
- customto give a pale yellow residue, which
- customwas purified on silica gel column chromatography
- washeluting with dichloromethane/methanol (9:1)
Sources & evidence
- ORD record
- ord-b6627e6dc7c54704a3e94a758f8ef794
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08912220B2
Reaction notes
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