Benzenesulfonyl chloride, 3,4-dichloro- → [1-(3,4-dichloro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester

HRID 1254847Notes

Reaction equation

HRID 1254847 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:17])[CH2:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[CH3:16].C1COCC1.CN(C=O)C.[Cl:28][C:29]1[CH:30]=[C:31]([S:36](Cl)(=[O:38])=[O:37])[CH:32]=[CH:33][C:34]=1[Cl:35]>C1COCC1>[CH3:3][O:4][C:5](=[O:17])[CH2:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([S:36]([C:31]2[CH:32]=[CH:33][C:34]([Cl:35])=[C:29]([Cl:28])[CH:30]=2)(=[O:38])=[O:37])[C:8]=1[CH3:16]

Participants

6

Reactant 4

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 24758Sodium hydrideHCID 21974620tetrahydrofuran N,N-dimethylformamideHCID 67218699methyl 2-(2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetate

Product 1

HCID 67219036[1-(3,4-dichloro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooled stirring suspension of NaH (60% dispersion in mineral oil; 63 mg, 1.6 mmol) in THF (3 mL) is added a solution of (2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester (200 mg, 1 mmol) in 3:1 THF/DMF (4 mL). After 45 minutes, a solution of 3,4-dichloro-benzenesulfonyl chloride (214 μL, 1.4 mmol) in THF (3 mL) is added. After 10 minutes, the reaction mixture is added to ice/water and extracted with EtOAc. The organic layer is washed with brine and evaporated. The crude product is purified by flash chromatography (3:1 iso-hexane/EtOAc elution), to afford [1-(3,4-dichloro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester; MH+=413.

Workup

  1. waitAfter 10 minutes
  2. extractionextracted with EtOAc
  3. washThe organic layer is washed with brine
  4. customevaporated
  5. customThe crude product is purified by flash chromatography (3:1 iso-hexane/EtOAc elution)

Sources & evidence

ORD record
ord-d6f1c167228e4cc495aea47ef01632a0
Source dataset
uspto-grants-2013_06
Patent number
US08455645B2

Reaction notes

Loading…