4-(Chloromethyl)-1-methoxy-2-(trifluoromethyl)benzene → 2-(7-(4-Methoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid
Reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH:13]([CH2:14][C:15]([O:17]C(C)(C)C)=[O:16])[C:6]3=[CH:5][C:4]=2[CH:3]=1.Cl[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([C:32]([F:35])([F:34])[F:33])[CH:25]=1>>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][O:1][C:2]2[CH:10]=[CH:9][C:8]3[N:7]4[CH2:11][CH2:12][CH:13]([CH2:14][C:15]([OH:17])=[O:16])[C:6]4=[CH:5][C:4]=3[CH:3]=2)=[CH:25][C:26]=1[C:32]([F:33])([F:35])[F:34]Participants
3
Procedure
From tert-butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate and 4-(chloromethyl)-1-methoxy-2-(trifluoromethyl)benzene, the title compound was prepared using a similar method to the one described in Example 1.48, Step B. LCMS m/z=420.1 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 2.31-2.39 (m, 1H), 2.50 (dd, J=16.3, 9.9 Hz, 1H), 2.75 (dd, J=16.3, 4.4 Hz, 1H), 2.83-2.93 (m, 1H), 3.59-3.67 (m, 1H), 3.85 (s, 3H), 3.95-4.05 (m, 2H), 4.06-4.14 (m, 2H), 5.30 (s, 1H), 6.67-6.74 (m, 2H), 6.86 (d, J=8.6 Hz, 1H), 7.08 (d, J=8.5 Hz, 1H), 7.28 (d, J=2.0 Hz, 1H), 7.43 (d, J=2.0 Hz, 1H).
Sources & evidence
- ORD record
- ord-af1a11d5ee5841c88c0ce99590e8accf
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108969B2
Reaction notes
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