Carbon Dioxide → HCID 44475513, compound

HRID 733663Notes

Reaction equation

HRID 733663 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]>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

6

Reactant 3

HCID 280Carbon DioxideHCID 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 (200 mg) in dry tetrahydrofuran (4 ml) at −40° C. under an atmosphere of nitrogen, was added dropwise, a solution of isopropylmagnesium chloride (2M in tetrahydrofuran, 600 ul) and the solution stirred at −40° C. for 15 minutes. The solution was saturated with a stream of carbon dioxide gas and then diluted with ethyl acetate. The organic was extracted with saturated ammonium chloride followed by 1N sodium hydroxide solution. The combined aqueous was then acidified to pH1 with concentrated hydrochloric acid to afford a precipitate. The precipitate was filtered and washed with water until neutral. The solid was then sucked dry and dried over sodium hydroxide at 50° C. to afford the title compound (86 mg).

Workup

  1. extractionThe organic was extracted with saturated ammonium chloride
  2. customto afford a precipitate
  3. filtrationThe precipitate was filtered
  4. washwashed with water until neutral
  5. customThe solid was then sucked dry
  6. dry with materialdried over sodium hydroxide at 50° C.

Sources & evidence

ORD record
ord-73b9814ee4d8445bbf446fe691597bef
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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