Methyl iodide → HCID 67219256, compound

HRID 1445571Notes

Reaction equation

HRID 1445571 reaction equation
[CH:1](NC(C)C)(C)C.[Li]CCCC.[CH3:13][O:14][C:15](=[O:38])[CH2:16][C:17]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[N:19]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=2)(=[O:28])=[O:27])[C:18]=1[CH3:37].CI>C1COCC1>[CH3:13][O:14][C:15](=[O:38])[CH:16]([C:17]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[N:19]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=2)(=[O:27])=[O:28])[C:18]=1[CH3:37])[CH3:1]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 67219036[1-(3,4-dichloro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl esterHCID 178418339Butyllithium

Product 1

HCID 67219256HCID 67219256, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring solution of diisopropylamine (34 μL, 0.24 mmol) in THF (1 mL), at −78° C., is added a 2.5M solution of n-BuLi in hexanes (105 μL, 0.26 mmol). After 20 minutes, a solution of [1-(3,4-dichloro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester (Method B; 100 mg, 0.24 mmol) and MeI (15.2 μL, 0.24 mmol) in THF (1 mL) is added. The reaction is continued for 30 minutes, then allowed to warm to room temperature. The reaction mixture is evaporated to dryness and purified by flash chromatography (4:1 iso-hexane/EtOAc elution), to afford 2-[1-(3,4-dichloro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-propionic acid methyl ester; MH+=427.

Workup

  1. waitThe reaction is continued for 30 minutes
  2. customThe reaction mixture is evaporated to dryness
  3. custompurified by flash chromatography (4:1 iso-hexane/EtOAc elution)

Sources & evidence

ORD record
ord-3f1473a02de048c2b1975b42f5a801d9
Source dataset
uspto-grants-2010_02
Patent number
US07666878B2

Reaction notes

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