Triphenylphosphine → 2-(6-chloro-5-methyl-1H-indol-3-yl)ethanamine

HRID 925317Notes

Reaction equation

HRID 925317 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][C:11]([Cl:16])=[C:12]([CH3:15])[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:16][C:11]1[CH:10]=[C:9]2[C:14]([C:6]([CH2:5][CH2:4][NH2:1])=[CH:7][NH:8]2)=[CH:13][C:12]=1[CH3:15]

Participants

6

Reactant 2

HCID 11776TriphenylphosphineHCID 866638373-(2-azidoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indole

Product 1

HCID 668321552-(6-chloro-5-methyl-1H-indol-3-yl)ethanamine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

2-(6-chloro-5-methyl-1H-indol-3-yl)ethanamine was prepared according to method D Step V with 3-(2-azidoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indole (0.654 g; 1.87 mmol) and triphenylphosphine (0.737 g; 2.81 mmol) in methanol (10 mL) and tetrabutylamonium fluoride (5.62 mL 1M) in THF (stirred for 36 hours).

Sources & evidence

ORD record
ord-1e0b12811f2843d788b87ddd7459b3cf
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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