Water → HCID 12018133, compound

HRID 1017570Notes

Reaction equation

HRID 1017570 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:30])[NH:13][C:14](=[O:29])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][CH2:25][N:26]=[N+]=[N-])[CH:17]=2)=[CH:3]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:30])[NH:13][C:14](=[O:29])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][CH2:25][NH2:26])[CH:17]=2)=[CH:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 12018143HCID 12018143, compound

Product 1

HCID 12018133HCID 12018133, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1-methylindol-3-yl)-4-[3-(3-azidopropyloxy)phenyl]-1H-pyrrole-2,5-dione (0.4 g, 1 mmol) in THF (20 mL) was added Ph3P (0.25 g, 1.1 eq.), followed by the H2O (0.017 mL). The resulting mixture was stirred at room temperature for 48 h and then concentrated in vacuo. The residue was purified on a silica gel column with 8% (10% NH4OH in methanol) in CH2Cl2 to give 3-(1-methylindol-3-yl)-4-[3-(3-aminopropyloxy)-phenyl]-1H-pyrrole-2,5-dione (0.35 g) which was converted to HCl salt and recrystalized to give 3-(1-methylindol-3-yl)-4-[3-(3-aminopropyloxy)phenyl]-1H-pyrrole-2,5-dione (0.21 g) as the HCl salt.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified on a silica gel column with 8% (10% NH4OH in methanol) in CH2Cl2

Sources & evidence

ORD record
ord-07e1498ecd2c4f448a4b97cc56cb29f8
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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