Triphenylphosphine → HCID 18993162, compound

HRID 375642Notes

Reaction equation

HRID 375642 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]=[N+]=[N-])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][NH2:22])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:3]1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 18993251HCID 18993251, compound

Product 1

HCID 18993162HCID 18993162, compoundYield 270.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 1-methyl-3-[4-(azidomethyl)phenylsulfonylamino]indole (674 mg, 1.97 mmol), prepared as in step 1, in 8:2 THF/H2O (10 mL) was added triphenylphosphine (1.03 g, 3.9 mmol) and the reaction mixture was stirred for 17 hours at ambient temperature. The reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and brine. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo to give 1-methyl-3-[4-(aminomethyl)phenylsulfonylamino]indole (1.68 g) as a yellow-orange foam.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a9e769c7efe47858bd2deb596f3c299
Source dataset
uspto-grants-1996_01
Patent number
US05486525

Reaction notes

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