1-(Bromomethyl)-4-fluoro-2-methylbenzene → 2-Tert-butoxy-2-[1-[(4-fluoro-2-methyl-phenyl)methyl]-6-methyl-4-(p-tolyl)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:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)=[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].Br[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=1[CH3:37]>>[C:1]([O:5][CH:6]([C:11]1[C:12]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)=[C:13]2[CH:20]=[CH:19][N:18]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=3[CH3:37])[C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([OH:9])=[O:8])([CH3:3])([CH3:4])[CH3:2]Participants
3
Procedure
The title compound was prepared from methyl 2-(tert-butoxy)-2-(6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate and 1-(bromomethyl)-4-fluoro-2-methylbenzene in a manner similar to that described in Example 25 as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) d=7.65 (d, J=7.0 Hz, 1 H), 7.41 (d, J=7.0 Hz, 1 H), 7.37-7.30 (m, 2 H), 7.03 (dd, J=6.0, 8.3 Hz, 1 H), 6.96-6.83 (m, 3 H), 6.22 (d, J=3.5 Hz, 1 H), 5.58-5.49 (m, 2 H), 5.44-5.37 (m, 1 H), 2.76 (s, 3 H), 2.47 (s, 3 H), 2.32 (s, 3 H), 0.95 (s, 9 H); LCMS (m/z) ES+=475 (M+1).
Sources & evidence
- ORD record
- ord-490eaadabead493fb869b156c5b0e947
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609653B2
Reaction notes
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