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

HRID 925312Notes

Reaction equation

HRID 925312 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-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[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

6

Reactant 2

HCID 11776TriphenylphosphineHCID 866638363-(2-azidoethyl)-2-(triethylsilyl)-5-(trifluoromethyl)-1H-indole

Product 1

HCID 120301362-(5-(trifluoromethyl)-1H-indol-3-yl)ethanamine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

2-(5-(trifluoromethyl)-1H-indol-3-yl)ethanamine was prepared according to method D Step V with 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) and tetrabutylamonium fluoride (3.26 mL, 1M) in THF (stirred for 36 hours).

Sources & evidence

ORD record
ord-ee31186d497942e99f819ff1c4cf7e95
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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