3-Fluoro-4-methylbenzyl bromide → 2-Tert-butoxy-2-[4-chroman-6-yl-1-[(3-fluoro-4-methyl-phenyl)methyl]-6-methyl-pyrrolo[2,3-b]pyridin-5-yl]acetic acid
Reaction equation
[C:1]([O:5][CH:6]([C:11]1[C:12]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[O:27][CH2:26][CH2:25][CH2:24]3)=[C:13]2[CH:20]=[CH:19][NH:18][C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[F:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[CH3:40])[CH2:35]Br>>[C:1]([O:5][CH:6]([C:11]1[C:12]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[O:27][CH2:26][CH2:25][CH2:24]3)=[C:13]2[CH:20]=[CH:19][N:18]([CH2:35][C:34]3[CH:37]=[CH:38][C:39]([CH3:40])=[C:32]([F:31])[CH:33]=3)[C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]Participants
3
Procedure
The title compound was prepared in a manner similar to that described in Example 27, Step H from methyl 2-(tert-butoxy)-2-(4-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate and 3-fluoro-4-methylbenzyl bromide. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.50-7.42 (m, 1 H), 7.21 (dd, J=1.9, 10.8 Hz, 1 H), 7.14 (t, J=7.7 Hz, 1 H), 7.05 (t, J=3.4 Hz, 1 H), 6.99-6.89 (m, 3 H), 6.28 (dd, J=3.5, 11.5 Hz, 1 H), 5.60-5.56 (m, 1 H), 5.56-5.39 (m, 2 H), 4.28 (t, J=4.5 Hz, 2 H), 2.95-2.80 (m, 2 H), 2.76 (s, 3 H), 2.25 (s, 3 H), 2.09 (d, 2 H), 1.03-0.88 (s, 9 H); LC/MS (m/z) ES+=517.38 (M+1).
Sources & evidence
- ORD record
- ord-76ecf815d1ad4411b66f8522fa0751f1
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609653B2
Reaction notes
Loading…