2-Chloro-6-fluoro-3-methylbenzyl bromide → HCID 71209397, compound

HRID 1912574Notes

Reaction equation

HRID 1912574 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].[Cl:31][C:32]1[C:39]([CH3:40])=[CH:38][CH:37]=[C:36]([F:41])[C:33]=1[CH2:34]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]([CH2:34][C:33]3[C:36]([F:41])=[CH:37][CH:38]=[C:39]([CH3:40])[C:32]=3[Cl:31])[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 27736792-Chloro-6-fluoro-3-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 71209397HCID 71209397, 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 2-chloro-6-fluoro-3-methylbenzyl bromide. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.49-7.40 (m, 1 H), 7.26-7.17 (m, 2 H), 7.02-6.88 (m, 3 H), 6.20-6.12 (m, 1 H), 5.73-5.66 (m, 1 H), 5.66-5.55 (m, 2 H), 4.30-4.24 (m, 2 H), 2.92-2.78 (m, 2 H), 2.74 (s, 3 H), 2.38 (s, 3 H), 2.12-2.06 (m, 2 H), 1.01-0.92 (s, 9 H); LC/MS (m/z) ES+=551.36 (M+1).

Sources & evidence

ORD record
ord-ce1bef00f74744ec983f86d1cfe3ae20
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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