2-Fluoro-5-(trifluoromethyl)aniline → HCID 178422788, compound

HRID 1898411Notes

Reaction equation

HRID 1898411 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][NH:5][C:6]1[NH:10][C:9]2[C:11]3[CH2:12][C:13]([CH3:23])([CH3:22])[O:14][C:15]=3[C:16]([C:18](OC)=[O:19])=[CH:17][C:8]=2[N:7]=1.[F:28][C:29]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][C:30]=1[NH2:31].C[Al](C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][NH:5][C:6]1[NH:10][C:9]2[C:11]3[CH2:12][C:13]([CH3:23])([CH3:22])[O:14][C:15]=3[C:16]([C:18]([NH:31][C:30]3[CH:32]=[C:33]([C:36]([F:37])([F:38])[F:39])[CH:34]=[CH:35][C:29]=3[F:28])=[O:19])=[CH:17][C:8]=2[N:7]=1

Participants

5

Reactant 3

HCID 1363492-Fluoro-5-(trifluoromethyl)anilineHCID 16682925TrimethylaluminumHCID 178497000HCID 178497000, compound

Product 1

HCID 178422788HCID 178422788, compoundYield 4.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared following the procedure described for Example-137 using methyl 2-((2-chlorobenzyl)amino)-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylate (Intermediate-52, 0.200 g, 0.519 mmol), 2-fluoro-5-trifluoromethyl aniline (0.237 g, 1.0389 mmol), trimethyl aluminium (2M solution in toluene) (0.5 mL) and dry toluene (5.0 mL). The obtained crude was purified by column chromatography eluting with 0.5% DCM:MeOH to afford 0.013 g of the desired product. 1HNMR (DMSO-d6): δ 1.55 (s, 6H), 3.14 (s, 2H), 4.61 (m, 2H), 7.32 (m, 2H), 7.40 (m, 1H), 7.49-7.62 (m, 5H), 7.69 (m, 1H), 8.93 (d, J=6.3 Hz, 1H), 10.34 (bs, 1H), 11.00 (bs, 1H). [M+H]+: 533.08.

Workup

  1. customThe title compound was prepared
  2. customThe obtained crude
  3. customwas purified by column chromatography
  4. washeluting with 0.5% DCM

Sources & evidence

ORD record
ord-1a1017d1bb4c40f695e1e47f7172540f
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

Loading…