Diisopropylethylamine → 5-((5-Methylpyridin-2-yl)methoxy)-2-nitro-N-((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)aniline

HRID 1848748Notes

Reaction equation

HRID 1848748 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][NH2:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.F[C:20]1[CH:21]=[C:22]([CH:32]=[CH:33][C:34]=1[N+:35]([O-:37])=[O:36])[O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][N:26]=1.CCN(C(C)C)C(C)C>C(#N)C>[CH3:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][O:23][C:22]2[CH:21]=[CH:20][C:34]([N+:35]([O-:37])=[O:36])=[C:33]([CH:32]=2)[NH:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:17])([F:18])[F:1])=[CH:8][CH:7]=3)=[CH:10][CH:11]=2)=[N:26][CH:27]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 37291554-(4-TRIFLUOROMETHYLPHENYL)BENZYLAMINEHCID 904110842-((3-Fluoro-4-nitrophenoxy)methyl)-5-methylpyridine

Product 1

HCID 904104425-((5-Methylpyridin-2-yl)methoxy)-2-nitro-N-((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)anilineYield 73.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
80 °C

Procedure

To a flask containing (4′-(trifluoromethyl)-[1,1′-biphenyl]-4-yl)methanamine (107 g, 406 mmol) and 2-((3-fluoro-4-nitrophenoxy)methyl)-5-methylpyridine (114 g, 406 mmol) in acetonitrile (900 mL) was added DIPEA (106 mL, 610 mmol). The stirred mixture was then warmed to 80° Celsius and held for 7 h. After cooling to RT, the resulting slurry was diluted with acetonitrile (300 mL), filtered and the resulting solids were washed with acetonitrile (200 mL). The solids were dried in a vacuum oven at 75° Celsius for 3 h to give the title compound (147.5 g, 73%). MS (ESI): mass calcd. for C27H22F3N3O3, 493.2; m/z found, 494.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.71 (bs, 1H), 8.38 (s, 1H), 8.17 (d, J=9.5, 1H), 7.69 (s, 4H), 7.58 (d, J=7.8, 2H), 7.49 (d, J=7.8, 1H), 7.43 (d, J=7.8, 2H), 7.29 (d, J=8.0, 1H), 6.35 (d, J=9.6, 1H), 6.29 (s, 1H), 5.13 (s, 2H), 4.54 (d, J=5.7, 2H), 2.30 (s, 3H).

Workup

  1. temperatureAfter cooling to RT
  2. filtrationfiltered
  3. washthe resulting solids were washed with acetonitrile (200 mL)
  4. customThe solids were dried in a vacuum oven at 75° Celsius for 3 h

Sources & evidence

ORD record
ord-ed2d8070bb904c89b50f67d4d6a35785
Source dataset
uspto-grants-2015_02
Patent number
US08952177B2

Reaction notes

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