3,4,5-Trifluorobenzyl bromide → 2-Tert-butoxy-2-[4-chroman-6-yl-6-methyl-1-[(3,4,5-trifluorophenyl)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]=[C:38]([F:41])[C:39]=1[F: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:33]=[C:32]([F:31])[C:39]([F:40])=[C:38]([F:41])[CH:37]=3)[C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]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 3,4,5-trifluorobenzyl bromide. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.50-7.43 (m, 1 H), 7.24-7.17 (m, 1 H), 7.07 (t, J=3.0 Hz, 1 H), 6.97-6.87 (m, 3 H), 6.35 (dd, J=3.3, 11.3 Hz, 1 H), 5.60-5.42 (m, 3 H), 4.29 (t, J=4.8 Hz, 2 H), 2.92-2.80 (m, 2 H), 2.76 (s, 3 H), 2.15-2.07 (m, 2 H), 1.01-0.91 (s, 9 H); LC/MS (m/z) ES+=539.34 (M+1).
Sources & evidence
- ORD record
- ord-d3e3c8c7d25d4aa49e9a92ffe99ce9b9
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609653B2
Reaction notes
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