Water → HCID 67055472, compound

HRID 1821532Notes

Reaction equation

HRID 1821532 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:20][O:21][C:22](=[O:64])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[C:38]([Cl:41])[CH:39]=3)[N:34]([CH:42]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:33]=2[CH2:55][CH2:56][N:57]=[N+]=[N-])=[CH:25][C:24]=1[O:60][CH:61]([CH3:63])[CH3:62].O>C1COCC1>[CH3:20][O:21][C:22](=[O:64])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[C:38]([Cl:41])[CH:39]=3)[N:34]([CH:42]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:33]=2[CH2:55][CH2:56][NH2:57])=[CH:25][C:24]=1[O:60][CH:61]([CH3:62])[CH3:63]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86588916HCID 86588916, compound

Product 1

HCID 67055472HCID 67055472, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ph3P (polymer support: 3 mmol Ph3P/gram) (0.100 g, 0.30 mmol) was added to a solution of the azide from Step 6 (0.100 g, 0.16 mmol) in THF (2 mL). Reaction was stirred at room temperature for 24 hours. Then water (0.5 mL) was added and reaction was stirred at room temperature overnight. Reaction solution was filtered and the filtrate was concentrated by rotary evaporation. The resulting residue was purified with silica gel prep plates and 2% MeOH in dichloromethane as eluent. Obtained 0.020 g of 4-{2-[2-(2-Amino-ethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]-ethoxy}-2-isopropoxy-benzoic acid methyl ester in 21% yield.

Workup

  1. customReaction
  2. customreaction
  3. stirringwas stirred at room temperature overnight
  4. customReaction solution
  5. filtrationwas filtered
  6. concentrationthe filtrate was concentrated by rotary evaporation
  7. customThe resulting residue was purified with silica gel prep plates and 2% MeOH in dichloromethane as eluent

Sources & evidence

ORD record
ord-f88a9c4a6c6647c48efa5dee3d69051a
Source dataset
uspto-grants-2009_10
Patent number
US07605156B2

Reaction notes

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