1-(Bromomethyl)-3-chloro-2-fluorobenzene → HCID 71209381, compound

HRID 1912562Notes

Reaction equation

HRID 1912562 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:33]([F:40])=[C:34]([CH:37]=[CH:38][CH:39]=1)[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:37]=[CH:38][CH:39]=[C:32]([Cl:31])[C:33]=3[F: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 5228271-(Bromomethyl)-3-chloro-2-fluorobenzeneHCID 71209024methyl 2-(tert-butoxy)-2-(4-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate

Product 1

HCID 71209381HCID 71209381, 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 3-chloro-2-fluorobenzyl bromide. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.49-7.42 (m, 1 H), 7.38-7.31 (m, 1 H), 7.24-7.11 (m, 3 H), 7.06-7.00 (m, 1 H), 6.94 (dd, J=4.5, 8.4 Hz, 1 H), 6.30 (dd, J=3.5, 11.5 Hz, 1 H), 5.71-5.52 (m, 3H), 4.33-4.26 (m, 2 H), 2.95-2.81 (m, 2 H), 2.76 (s, 3 H), 2.14-2.03 (m, 2 H), 1.01-0.91 (s, 9 H); LC/MS (m/z) ES+=537.4 (M+1).

Sources & evidence

ORD record
ord-02a9d9d278bc4211b0b7c712f624768d
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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