Triphenylphosphine → 2-(5,6-Dichloro-1H-indol-3-yl)ethanamine

HRID 925321Notes

Reaction equation

HRID 925321 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][C:11]([Cl:16])=[C:12]([Cl:15])[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>[Cl:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[Cl:16])[NH:8][CH:7]=[C:6]2[CH2:5][CH2:4][NH2:1]

Participants

6

Reactant 2

HCID 11776TriphenylphosphineHCID 866993923-(2-Azidoethyl)-5,6-dichloro-2-(triethylsilyl)-1H-indole

Product 1

HCID 133016902-(5,6-Dichloro-1H-indol-3-yl)ethanamine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

2-(5,6-dichloro-1H-indol-3-yl)ethanamine was prepared according to method D Step V with 3-(2-azidoethyl)-5,6-dichloro-2-(triethylsilyl)-1H-indole (0.497 g; 1.35 mmol) and triphenylphosphine (0.529 g; 1.35 mmol) in methanol (10 mL) and tetrabutylamonium fluoride (4.04 mL 1M) in THF (stirred for 36 hours).

Sources & evidence

ORD record
ord-eea1b11ecb0840e19cdb5fd1c520bb90
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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