Hydrochloric Acid → HCID 46865661, compound

HRID 1253913Notes

Reaction equation

HRID 1253913 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][C:11]3[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=3)[C:14]([OH:16])=[O:15])[CH:8]=2)[CH:3]=[CH:2]1.I[C:21]1[CH:22]=[C:23]([O:27][CH3:28])[CH:24]=[CH:25][CH:26]=1.[OH-].[K+].N#N.[OH-].[Na+].Cl>CS(C)=O.O>[CH3:28][O:27][C:23]1[CH:22]=[C:21]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][C:11]4[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=4)[C:14]([OH:16])=[O:15])[CH:8]=3)[CH:3]=[CH:2]2)[CH:26]=[CH:25][CH:24]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 69839Benzene, 1-iodo-3-methoxy-HCID 46882002HCID 46882002, compound

Product 1

HCID 46865661HCID 46865661, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

The acid, 3-((1H-indol-6-yl)methyl)benzoic acid, 20 mg, was dissolved in 4 ml DMSO, and 18 mg 3-iodoanisole, 12 mg potassium hydroxide and 5 mg Cu2O catalyst were added. The mixture was protected by N2 and stirred for 24 hours at 135° C. After cooling to room temperature, 1 ml 25% NaOH in H2O was added, The mixture was stirred for 3 hours at room temperature, then adjusted to pH 3.0 using 2M HCl. The solution was extracted with CH2Cl2, 3×15 ml. The organic solvent was combined and dried with Na2SO4, then evaporated to dryness. The final product was purified by HPLC using acetonitrile/H2O as eluent. The acetonitrile was removed from the eluent, the eluent frozen and lyophilized. After lyophilization, 5.0 mg of the target compound was obtained as a grey powder.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringThe mixture was stirred for 3 hours at room temperature
  3. extractionThe solution was extracted with CH2Cl2, 3×15 ml
  4. dry with materialdried with Na2SO4
  5. customevaporated to dryness
  6. customThe final product was purified by HPLC
  7. customThe acetonitrile was removed from the eluent
  8. temperaturethe eluent frozen

Sources & evidence

ORD record
ord-9d398f0801a4476483bce7fde64b1139
Source dataset
uspto-grants-2013_06
Patent number
US08455516B2

Reaction notes

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