3-Amino-2-fluorobenzotrifluoride → HCID 178422753, compound

HRID 1898434Notes

Reaction equation

HRID 1898434 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: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]([C:36]([F:39])([F:38])[F:37])=[CH:34][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]([F: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][CH:34]=[C:35]([C:36]([F:37])([F:38])[F:39])[C:29]=3[F:28])=[O:26])=[CH:15][C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 1455693-Amino-2-fluorobenzotrifluorideHCID 16682925TrimethylaluminumHCID 178496994HCID 178496994, compound

Product 1

HCID 178422753HCID 178422753, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared following the procedure described for Example-137 using methyl 2-[(2-chloro-6-fluorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylate (Step-1 of Intermediate-15, 0.100 g, 0.256 mmol), 2-fluoro-3-(trifluoromethyl)aniline (0.068 g, 0.379 mmol), trimethyl aluminium (2M solution in toluene) (0.5 mL) and dry toluene (5.0 mL) to afford 0.050 g of the desired product. 1HNMR (DMSO-d6): δ 1.56 (s, 6H), 3.13 (s, 2H), 7.32 (m, 2H), 7.42-7.45 (m, 4H), 8.76 (m, 1H), 10.20 (s, 1H), 11.20 (s, 2H); MS [M+H]+: 537.19.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-e1c6840611414c81aadd18f3c2ad15ee
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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