Carbon Dioxide → HCID 44475513, compound

HRID 733667Notes

Reaction equation

HRID 733667 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2=[C:13]([Cl:18])[N:14]=[CH:15][C:16](I)=[C:11]2[C:10]([CH3:19])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Mg]Cl)(C)C.[C:25](=[O:27])=[O:26].[O-]S([O-])(=O)=O.[Ca+2]>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:12]2[C:13]([Cl:18])=[N:14][CH:15]=[C:16]([C:25]([OH:27])=[O:26])[C:11]=2[C:10]([CH3:19])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 24497Calcium SulfateHCID 444755121,1-Dimethylethyl 7-chloro-4-iodo-3-methyl-1H-pyrrolo[2,3-c]pyridine-1-carboxylateHCID 178418918HCID 178418918, compound

Product 1

HCID 44475513HCID 44475513, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-chloro-4-iodo-3-methyl-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester (2 g) in dry tetrahydrofuran (40 ml) was added 4 A molecular sieves. The solution was stirred at room temperature for 15 minutes then cooled to 40° C. Under an atmosphere of nitrogen was added dropwise, a solution of isopropylmagnesium chloride (2M in tetrahydrofuran, 5.4 ml) and the solution stirred at −40° C. for 10 minutes. The solution was saturated with a stream of carbon dioxide gas which had been passed through a column of Drierite and then diluted with ethyl acetate. The organic was extracted with 1N sodium hydroxide solution until complete extraction and the combined aqueous was then acidified to pH1 with concentrated hydrochloric acid. The acidified aqueous was extracted twice with ethyl acetate which was combined and washed with water until neutral. The ethyl acetate layer was then dried (MgSO4) and evaporated to give a solid. The solid was triturated with isohexane, filtered off and washed with isohexane. The solid was sucked dry then dried at 50° C. under vacuum to afford the title compound (1.22 g).

Workup

  1. temperaturethen cooled to 40° C
  2. additionUnder an atmosphere of nitrogen was added dropwise
  3. extractionThe organic was extracted with 1N sodium hydroxide solution until complete extraction
  4. extractionThe acidified aqueous was extracted twice with ethyl acetate which
  5. washwashed with water until neutral
  6. dry with materialThe ethyl acetate layer was then dried (MgSO4)
  7. customevaporated
  8. customto give a solid
  9. customThe solid was triturated with isohexane
  10. filtrationfiltered off
  11. washwashed with isohexane
  12. customThe solid was sucked dry
  13. customthen dried at 50° C. under vacuum

Sources & evidence

ORD record
ord-c8e1269a978e4448ae4af9bba2d5b397
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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