2,3,4-Trifluoroaniline → HCID 178425056, compound

HRID 1898467Notes

Reaction equation

HRID 1898467 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24]([O:26]C)=O)=[CH:15][C:13]=2[N:14]=1.[F:28][C:29]1[C:35]([F:36])=[C:34]([F:37])[CH:33]=[CH:32][C:30]=1[NH2:31].C[Al](C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24]([NH:31][C:30]3[CH:32]=[CH:33][C:34]([F:37])=[C:35]([F:36])[C:29]=3[F:28])=[O:26])=[CH:15][C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 774682,3,4-TrifluoroanilineHCID 16682925TrimethylaluminumHCID 178496983HCID 178496983, compound

Product 1

HCID 178425056HCID 178425056, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared by following the procedure as described for Example-137 by using methyl 2-[(2-chloro-6-methylphenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylate (Step-1 of Intermediate-35, 0.200 g, 0.414 mmol) and 2,3,4-trifluoroaniline (0.090 g, 0.602 mmol), trimethyl aluminium (2M solution in toluene) (1 mL) and dry toluene (5.0 mL) to afford 0.100 g of the desired product. 1HNMR (DMSO-d6): δ 1.55 (s, 6H), 2.24 (s, 3H), 3.13 (s, 2H), 7.25-7.43 (m, 4H), 7.52 (s, 1H), 8.24 (m, 1H), 9.10 (m, 1H), 10.06 (s, 1H), 10.96 (m, 1H): MS [M+H]+: 501.04.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-c011ccd7b28145cdadf012aee3d19de7
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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