Water → HCID 20598524, compound

HRID 1008635Notes

Reaction equation

HRID 1008635 reaction equation
[CH3:1][O:2][C:3](=[O:41])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:22])[CH:20]=3)[N:15]([CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:14]=2[CH2:36][CH2:37][N:38]=[N+]=[N-])=[CH:6][CH:5]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:41])[C:4]1[CH:5]=[CH:6][C:7]([NH:10][CH2:11][CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:22])[CH:20]=3)[N:15]([CH:23]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:14]=2[CH2:36][CH2:37][NH2:38])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86588911HCID 86588911, compound

Product 1

HCID 20598524HCID 20598524, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-{2-[2-(2-azido-ethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]-ethylamino}-benzoic acid methyl ester (400 mg, 0.709 mmol) in THF (4 mL) at 0° C. was added Ph3P (223 mg, 0.851 mmol) in portions. The reaction mixture was stirred at rt for 11 h and 35° C. for 4 h before water (50 μL) was added and stirring continued overnight. The reaction mixture was diluted with EtOAc, dried with MgSO4 and purified by flash column chromatography (EtOAc to 20% MeOH/EtOAc with 1% Et3N) to give the desired 4-{2-[2-(2-Amino-ethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]-ethylamino}-benzoic acid methyl ester (201 mg, 53%) as a solid.

Workup

  1. additionwas added
  2. dry with materialdried with MgSO4
  3. custompurified by flash column chromatography (EtOAc to 20% MeOH/EtOAc with 1% Et3N)

Sources & evidence

ORD record
ord-2754a7a9606948ad98b376b08ab28d9e
Source dataset
uspto-grants-2004_09
Patent number
US06797708B2

Reaction notes

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