2-(2-Bromoethoxy)-1,1,1-trifluoroethane → 2-Isopropyl-3,6-dimethoxy-5-[2-(2,2,2-trifluoro-ethoxy)-ethyl]-2,5-dihydropyrazine

HRID 1185928Notes

Reaction equation

HRID 1185928 reaction equation
[CH:1]([CH:4]1[C:9]([O:10][CH3:11])=[N:8][CH:7]([CH2:12][CH2:13]C(F)(F)F)[C:6]([O:18][CH3:19])=[N:5]1)([CH3:3])[CH3:2].BrCC[O:23][CH2:24][C:25]([F:28])([F:27])[F:26]>>[CH:1]([CH:4]1[C:9]([O:10][CH3:11])=[N:8][CH:7]([CH2:12][CH2:13][O:23][CH2:24][C:25]([F:28])([F:27])[F:26])[C:6]([O:18][CH3:19])=[N:5]1)([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 198289712-(2-Bromoethoxy)-1,1,1-trifluoroethaneHCID 666212022-Isopropyl-3,6-dimethoxy-5-(3,3,3-trifluoro-propyl)-2,5-dihydro-pyrazine

Product 1

HCID 666204602-Isopropyl-3,6-dimethoxy-5-[2-(2,2,2-trifluoro-ethoxy)-ethyl]-2,5-dihydropyrazineYield 65%

Procedure

This compound was made in 65% yield by the same procedure as 2-Isopropyl-3,6-dimethoxy-5-(3,3,3-trifluoro-propyl)-2,5-dihydro-pyrazine, substituting 1-Iodo-3 ,3 ,3-trifluoropropane with 2-(2-Bromoethoxy)-1,1,1-trifluoroethane. 1H-NMR: 400 MHz, (CDCl3) δ: 4.11-4.05 (m, 1H), 3.95 (t, J=3.5 Hz, 1H), 3.86-3.75 (m, 3H), 3.74-3.66 (m, 7H), 2.30-2.18 (m, 2H), 1.92-1.82 (m, 1H), 1.03 (d, J=6.9 Hz, 3H), 0.70 (d, J=6.8 Hz, 31-1) ppm.

Sources & evidence

ORD record
ord-c24125391ab140b38d726e8b95515ef1
Source dataset
uspto-grants-2014_03
Patent number
US08669234B2

Reaction notes

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