Water → HCID 67055472, compound

HRID 2237148Notes

Reaction equation

HRID 2237148 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-32180a35138945ee91261a0ae85a8a93
Source dataset
uspto-grants-2010_05
Patent number
US07713964B2

Reaction notes

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