Water → HCID 67055492, compound

HRID 603979Notes

Reaction equation

HRID 603979 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:20][O:21][C:22](=[O:62])[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][CH3:61].O>C1COCC1>[CH3:20][O:21][C:22](=[O:62])[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:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:33]=2[CH2:55][CH2:56][NH2:57])=[CH:25][C:24]=1[O:60][CH3:61]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86588914HCID 86588914, compound

Product 1

HCID 67055492HCID 67055492, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ph3P (polymer support: 3 mmol Ph3P/gram) (0.110 g, 0.33 mmol) was added to a solution of the azide from step 7 (0.110 g, 0.18 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 0.012 g of 4-{2-[2-(2-Amino-ethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]-ethoxy}-2-methoxy-benzoic acid methyl ester in 12% 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-00e795ff6ef2442b94da08d1ded9b54c
Source dataset
uspto-grants-2011_03
Patent number
US07906548B2

Reaction notes

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