5-Fluoro-2-methylbenzyl bromide → HCID 71209173, compound

HRID 1912575Notes

Reaction equation

HRID 1912575 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]=[CH:34][C:35]([CH3:40])=[C:36]([CH:39]=1)[CH2:37]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]([CH2:37][C:36]3[CH:39]=[C:32]([F:31])[CH:33]=[CH:34][C:35]=3[CH3:40])[C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 27746055-Fluoro-2-methylbenzyl bromideHCID 71209024methyl 2-(tert-butoxy)-2-(4-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate

Product 1

HCID 71209173HCID 71209173, compound

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 5-fluoro-2-methylbenzyl bromide. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.51-7.42 (m, 1 H), 7.26-7.21 (m, 1 H), 7.18-7.12 (m, 1 H), 6.98-6.85 (m, 3 H), 6.66 (dt, J=3.3, 9.5 Hz, 1 H), 6.25 (dd, J=3.5, 12.3 Hz, 1 H), 5.62-5.56 (m, 1 H), 5.47-5.34 (m, 2 H), 4.27 (t, J=5.0 Hz, 2 H), 2.94-2.77 (m, 2 H), 2.73-2.66 (m, 3 H), 2.31 (d, J=3.3 Hz, 3 H), 2.14-2.06 (m, 2 H), 1.01-0.91 (s, 9 H); LC/MS (m/z) ES+=517.31 (M+1).

Sources & evidence

ORD record
ord-087055a84b99444281e57117f5e02b83
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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