4-(Bromomethyl)-1-fluoro-2-methylbenzene → 2-(tert-butoxy)-2-(4-(chroman-6-yl)-1-(4-fluoro-3-methylbenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetic acid

HRID 1912554Notes

Reaction equation

HRID 1912554 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].Br[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([F:39])=[C:35]([CH3:40])[CH:34]=1>>[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]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[C:35]([CH3:40])[CH:34]=3)[C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([OH:9])=[O:8])([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 27781354-(Bromomethyl)-1-fluoro-2-methylbenzeneHCID 71209024methyl 2-(tert-butoxy)-2-(4-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate

Product 1

HCID 712094012-(tert-butoxy)-2-(4-(chroman-6-yl)-1-(4-fluoro-3-methylbenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetic acid

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 4-(bromomethyl)-1-fluoro-2-methylbenzene. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.50-7.43 (m, 1 H), 7.23-7.17 (m, 1 H), 7.17-7.03 (m, 3 H), 7.00-6.90 (m, 2 H), 6.30 (dd, J=3.3, 10.1 Hz, 1 H), 5.63-5.53 (m, 2 H), 5.49-5.38 (m, 1 H), 4.29 (t, J=4.9 Hz, 2 H), 2.97-2.82 (m, 2 H), 2.80 (s, 3 H), 2.25 (s, 3 H), 2.14-2.04 (m, 2 H), 1.03-0.91 (s, 9 H); LC/MS (m/z) ES+=517.38 (M+1).

Sources & evidence

ORD record
ord-7244841aa1aa40cf8cd282b800a84ab0
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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