Triethylamine → 5-[(3-Cyclohexyl-2-phenyl-pyrrolo[2,3-c]pyridin-6-yl)methyl]-3-[4-fluoro-2-(trifluoromethyl)phenyl]isoxazole

HRID 594930Notes

Reaction equation

HRID 594930 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][N:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:23][C:24]1[O:28][N:27]=[C:26]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=2[C:36]([F:39])([F:38])[F:37])[CH:25]=1.[OH-].[Na+].C(N(CC)CC)C>CN(C=O)C>[CH:1]1([C:7]2[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:9][C:10]3[C:15]=2[CH:14]=[CH:13][N:12]([CH2:23][C:24]2[O:28][N:27]=[C:26]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=4[C:36]([F:39])([F:37])[F:38])[CH:25]=2)[CH:11]=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 251897213-Cyclohexyl-2-phenyl-1H-pyrrolo[2,3-c]pyridineHCID 468639965-Chloromethyl-3-(4-fluoro-2-trifluoromethyl-phenyl)-isoxazole

Product 1

HCID 251897175-[(3-Cyclohexyl-2-phenyl-pyrrolo[2,3-c]pyridin-6-yl)methyl]-3-[4-fluoro-2-(trifluoromethyl)phenyl]isoxazoleYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-cyclohexyl-2-phenyl-1H-pyrrolo[2,3-c]pyridine (9 mg, 33 μmol) and 5-(chloromethyl)-3-(4-fluoro-2-(trifluoromethyl)phenyl)isoxazole (11 mg, 39 μmol) in DMF (326 μL) was added 10% aqueous NaOH (16 mL, 39 μmol). After stirring 12 h at room temperature, the reaction was neutralized with triethylamine and the crude purified by reverse phase HPLC to provide 4.5 mg (27%) of the title compound: 1H NMR (CD3OD, 300 MHz) δ 9.2 (s, 1H), 8.36 (s, 2H), 7.55-7.72 (m, 8H), 6.82 (s, 1H), 6.12 (s, 2H), 3.04 (m, 1H), 1.78-2.06 (m, 7H), 1.30-1.50 (m, 3H); LCMS found 520.3 (M++H, C30H26F4N3O requires 520.5).

Workup

  1. customthe crude purified by reverse phase HPLC

Sources & evidence

ORD record
ord-644a52a61c934558a1ccb59ab58f021e
Source dataset
uspto-grants-2016_01
Patent number
US09242983B2

Reaction notes

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