5-(Chloromethyl)-2-methoxybenzonitrile → 2-(7-(3-Cyano-4-methoxybenzyloxy)-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:25]=[CH:26][C:27]([O:32][CH3:33])=[C:28]([CH:31]=1)[C:29]#[N:30]>>[C:29]([C:28]1[CH:31]=[C:24]([CH:25]=[CH:26][C:27]=1[O:32][CH3:33])[CH2:23][O:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH:13]([CH2:14][C:15]([OH:17])=[O:16])[C:6]3=[CH:5][C:4]=2[CH:3]=1)#[N:30]Participants
3
Procedure
From tert-butyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate and 5-(chloromethyl)-2-methoxybenzonitrile, the title compound was prepared using a similar method to the one described in Example 1.16, Step A & B. LCMS m/z=377.4 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 2.28-2.37 (m, 1H), 2.68 (dd, J=16.4, 8.3 Hz, 1H), 2.87-2.98 (m, 2H), 3.73-3.81 (m, 1H), 3.94 (s, 3H), 3.99-4.06 (m, 1H), 4.11-4.18 (m, 1H), 5.02 (s, 2H), 6.13 (s, 1H), 6.85 (dd, J=8.7, 2.4 Hz, 1H), 6.98 (d, J=8.6 Hz, 1H), 7.07 (d, J=2.3 Hz, 1H), 7.15 (d, J=8.7 Hz, 1H), 7.64 (dd, J=8.6, 2.1 Hz, 1H), 7.66 (d, J=2.0 Hz, 1H).
Sources & evidence
- ORD record
- ord-39a73f7869894bc38eaf98498a64d58d
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108969B2
Reaction notes
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