Sodium Sulfate → N-(2-(4,5,6,7-Tetrafluoro-1H-indol-3-yl)ethyl)-3-(2,2,2-trifluoroethoxy)benzylamine

HRID 1666869Notes

Reaction equation

HRID 1666869 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:7]2[C:3]=1[C:4]([CH2:14][CH2:15][NH2:16])=[CH:5][NH:6]2.[F:17][C:18]([F:30])([F:29])[CH2:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(O)C>[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:7]2[C:3]=1[C:4]([CH2:14][CH2:15][NH:16][CH2:24][C:23]1[CH:26]=[CH:27][CH:28]=[C:21]([O:20][CH2:19][C:18]([F:17])([F:29])[F:30])[CH:22]=1)=[CH:5][NH:6]2

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 47709473-(2,2,2-Trifluoroethoxy)benzaldehydeHCID 15584731HCID 15584731, compound

Product 1

HCID 21071624N-(2-(4,5,6,7-Tetrafluoro-1H-indol-3-yl)ethyl)-3-(2,2,2-trifluoroethoxy)benzylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

By a method similar to Example 763, using 2-(4,5,6,7-tetrafluoro-1H-indol-3-yl)ethylamine (484 mg, 2.08 mmol), ethanol (45 mL), 3-(2,2,2-trifluoroethoxy)benzaldehyde (425 mg, 2.08 mmol), anhydrous sodium sulfate (3.5 g) sodium borohydride (236 mg, 6.24 mmol) to give the free base of the title compound as a straw colored solid. Recrystallize from methylene chloride to obtain the title compound: mp 107.2-108.2° C. 1H NMR (400 MHz, dmso-d6): 11.92 (br s, 1H), 7.32 (s, 2H), 6.95-6.99 (m, 2H), 6.87 (dd, 1H, J=2.4, 8.0 Hz) 4.68 (q, 2H, J=8.8 Hz), 3.70 (s, 2H), 2.88 (t, 2H, J=7.2 Hz) 2.75 (t, 2H, J=7.2 Hz). MS (ES+): m/e 421.1 (M+1). CHN (for C19H15F7N2O.1HCl.0.20H2O) calcd: C, 53.83; H, 3.66; N, 6.61. found: C, 53.75; H, 3.33; N, 6.

Sources & evidence

ORD record
ord-2aabd7ba6ac74eaeb7a8e2b50bb7a1a3
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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