2-Fluoro-5-(trifluoromethyl)aniline → HCID 178432353, compound

HRID 1898451Notes

Reaction equation

HRID 1898451 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[NH:22][C:21]2[C:16]3[N:17]=[C:18]([CH3:20])[O:19][C:15]=3[C:14]([C:23](OC)=[O:24])=[CH:13][C:12]=2[N:11]=1.[F:27][C:28]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][C:29]=1[NH2:30].C[Al](C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[NH:22][C:21]2[C:16]3[N:17]=[C:18]([CH3:20])[O:19][C:15]=3[C:14]([C:23]([NH:30][C:29]3[CH:31]=[C:32]([C:35]([F:36])([F:37])[F:38])[CH:33]=[CH:34][C:28]=3[F:27])=[O:24])=[CH:13][C:12]=2[N:11]=1

Participants

5

Reactant 3

HCID 1363492-Fluoro-5-(trifluoromethyl)anilineHCID 16682925TrimethylaluminumHCID 178496996HCID 178496996, compound

Product 1

HCID 178432353HCID 178432353, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared following the procedure as described for Example-185 using methyl 7-[(2-chloro-6-fluorophenyl)amino]-2-methyl-8H-imidazo[4,5-e][1,3]benzoxazole-4-carboxylate (Step-3 of Intermediate-56, 0.100 g, 0.266 mmol), 2-fluoro-5-trifluoromethylaniline (0.071 g, 0.125 mmol), trimethyl aluminium (2M solution in toluene) (0.5 mL) and dry toluene (5.0 mL) to afford 0.015 g of the desired product. 1HNMR (DMSO-d6): δ 2.72 (s, 3H), 7.41-7.47 (m, 3H), 7.63 (s, 2H), 7.76 (s, 1H), 8.54 (d, J=6.9 Hz, 1H), 9.45 (s, 1H), 9.92 (s, 1H), 11.71 (s, 1H); MS [M+H]+: 522.12.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-b9d9be4af2ae4fe2a15154d9e9e99b92
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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