Methyl iodide → HCID 67219256, compound

HRID 1254852Notes

Reaction equation

HRID 1254852 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-a9701903d2fb4ac68954fced6c8c2526
Source dataset
uspto-grants-2013_06
Patent number
US08455645B2

Reaction notes

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