1-Bromo-2-(2,2,2-trifluoroethoxy)benzene → 5-[3-Fluoro-2'-(2,2,2-trifluoroethoxy)biphenyl-4-yl]pyrazin-2-amine

HRID 1523986Notes

Reaction equation

HRID 1523986 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[C:17]1[N:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=1.[F:24][C:25]([F:36])([F:35])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1Br>>[F:1][C:2]1[CH:7]=[C:6]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[O:27][CH2:26][C:25]([F:24])([F:36])[F:35])[CH:5]=[CH:4][C:3]=1[C:17]1[N:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=1

Participants

3

Reactant 2

HCID 226154791-Bromo-2-(2,2,2-trifluoroethoxy)benzeneHCID 903122765-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-pyrazin-2-amine

Product 1

HCID 903141025-[3-Fluoro-2'-(2,2,2-trifluoroethoxy)biphenyl-4-yl]pyrazin-2-amine

Procedure

The title compound was prepared using analogous conditions to those described in Example 1 utilizing what 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazin-2-amine and 2-(2,2,2-trifluoroethoxy)bromobenzene. MS (ESI): mass calcd. for C18H13F4N3O, 363.10; m/z found, 363.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.39 (s, 1H), 8.03 (s, 1H), 7.91 (m, 1H), 7.56-7.34 (m, 4H), 7.25 (d, J=8.0, 1H), 7.16 (m, 1H), 6.71 (s, 2H), 4.82 (q, J=8.8, 2H).

Sources & evidence

ORD record
ord-5c7dc37bc260435693fbf5bd3c0ae239
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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