Triphenylphosphine → 2-(5-(trifluoromethyl)-1H-indol-3-yl)ethanamine

HRID 58628Notes

Reaction equation

[N:1]([CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([F:18])([F:17])[F:16])[CH:13]=2)[NH:8][C:7]=1[Si](CC)(CC)CC)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO>[F:17][C:15]([F:16])([F:18])[C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:5][CH2:4][NH2:1]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-(2-azidoethyl)-2-(triethylsilyl)-5-(trifluoromethyl)-1H-indole (0.400 g; 1.09 mmol) and triphenyl phosphine (0.427 g; 1.63 mmol) in methanol (5 mL) was stirred at 70° C. for 2 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in a solution of tetrabutylammonium fluoride (3.26 mL, 1M) in THF and stirred at room temperature for 36 hours and concentrated under reduced pressure to yield 2-(5-(trifluoromethyl)-1H-indol-3-yl)ethanamine, which was used without any further purification.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
dissolutionThe residue was dissolved in a solution of tetrabutylammonium fluoride (3.26 mL, 1M) in THF
stirringstirred at room temperature for 36 hours
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-defc60703a904772acaf92d208800366
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434722B2

Reaction notes

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