2,3-Difluoro-6-methoxybenzyl bromide → HCID 71209147, compound

HRID 1912567Notes

Reaction equation

HRID 1912567 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[C:35]([F:36])=[C:34]([F:37])[CH:33]=[CH:32][C:31]=1[O:38][CH3:39]>>[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[C:31]([O:38][CH3:39])=[CH:32][CH:33]=[C:34]([F:37])[C:35]=3[F:36])[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 49958612,3-Difluoro-6-methoxybenzyl bromideHCID 71209083Methyl 2-(tert-butoxy)-2-(6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate

Product 1

HCID 71209147HCID 71209147, compound

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 2-(bromomethyl)-3,4-difluoro-1-methoxybenzene in a manner similar to that described in Example 25 as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm=7.64 (d, J=7.0 Hz, 1 H), 7.43-7.38 (m, 1 H), 7.34 (d, J=7.4 Hz, 2 H), 7.12 (d, J=3.5 Hz, 1 H), 7.00 (dd, J=9.2, 10.1 Hz, 1 H), 6.73 (dd, J=6.4, 11.9 Hz, 1 H), 6.24 (d, J=3.5 Hz, 1 H), 5.54 (s, 1 H), 5.48 (d, J=6.0 Hz, 2 H), 3.86 (s, 3 H), 2.78 (s, 3 H), 2.47 (s, 3 H), 0.95 (s, 9 H); LCMS (m/z) ES+=509 (M+1).

Sources & evidence

ORD record
ord-22aff3c53dc64ce98d9c9ce9ee077c0d
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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