(2S)-2,5-Dihydro-2-isopropyl-3,6-dimethoxypyrazine → (2S,5R)-2,5-Dihydro-3,6-dimethoxy-2-isopropyl-5-(4'-bromo-2,5'-difluorobenzyl)pyrazine

HRID 1919483Notes

Reaction equation

HRID 1919483 reaction equation
[CH3:1][O:2][C:3]1[C@H:4]([CH:11]([CH3:13])[CH3:12])[N:5]=[C:6]([O:9][CH3:10])[CH2:7][N:8]=1.[Br:14][C:15]1[C:22]([F:23])=[CH:21][C:18]([CH2:19]Br)=[C:17]([F:24])[CH:16]=1>>[CH3:1][O:2][C:3]1[C@H:4]([CH:11]([CH3:13])[CH3:12])[N:5]=[C:6]([O:9][CH3:10])[C@@H:7]([CH2:19][C:18]2[CH:21]=[C:22]([F:23])[C:15]([Br:14])=[CH:16][C:17]=2[F:24])[N:8]=1

Participants

3

Reactant 2

HCID 736065(2S)-2,5-Dihydro-2-isopropyl-3,6-dimethoxypyrazineHCID 219112101-Bromo-4-(bromomethyl)-2,5-difluorobenzene

Product 1

HCID 67374536(2S,5R)-2,5-Dihydro-3,6-dimethoxy-2-isopropyl-5-(4'-bromo-2,5'-difluorobenzyl)pyrazineYield 88%

Procedure

The title compound (1.61 g) was prepared from 0.865 g (4.7 mmol) of (2S)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine and 1.5 g (5.2 mmol) of 4-bromo-2,5-difluorobenzyl bromide using the procedure described for Intermediate 2, Step A. 1H NMR (400 MHz, CDCl3) δ 7.21 (m, 1H), 6.97 (m, 1H), 4.25 (m, 1H), 3.78 (s, 3H), 3.70-3.64 (m, 4H), 3.25-3.18 (m, 1H), 2.96-2.90 (m, 1H), 2.25-2.16 (m, 1H), 1.01 (d, 3H, J=8 Hz), 0.65 (d, 3H, J=8 Hz).

Sources & evidence

ORD record
ord-d3a752fe7c914bcdada75150fd820dbc
Source dataset
uspto-grants-2012_05
Patent number
US08168637B2

Reaction notes

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