Hydrochloric Acid → HCID 86742936, compound

HRID 1722455Notes

Reaction equation

HRID 1722455 reaction equation
[CH2:1]([C:3]1([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3I)[CH3:2].Cl.N1C=C[CH:26]=[CH:25][CH:24]=1>>[CH2:1]([C:3]1([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[C:24]#[C:25][CH3:26])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 14146245HCID 14146245, compound

Product 1

HCID 86742936HCID 86742936, compound

Procedure

A mixture of 1-ethyl-8-iodo-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, methyl ester (5.93 g, 14.86 mmol), copper (I) methyl acetylide (3.05 g, 29.72 mmol), and 75 mL of dry pyridine was refluxed, under a flow of nitrogen, for 6 hours. The mixture was then poured into 100 mL of 1N HCl and the aqueous solution was extracted with ether. The combined extracts were washed with 1N HCl and saturated NaCl, dried over magnesium sulfate, filtered and concentrated to give the crude product. The material was purified by flash chromatography (15% ethyl acetate/hexane, silica gel) to give the pure title compound (2.16 g).

Workup

  1. temperaturewas refluxed, under a flow of nitrogen, for 6 hours
  2. extractionthe aqueous solution was extracted with ether
  3. washThe combined extracts were washed with 1N HCl and saturated NaCl
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customThe material was purified by flash chromatography (15% ethyl acetate/hexane, silica gel)

Sources & evidence

ORD record
ord-e2a7e75737074ea09e00b2ab42816c5c
Source dataset
uspto-grants-1989_08
Patent number
US04855445

Reaction notes

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