Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine | HCID 3513851 | — |
| Reactant | methyl 2-(2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetate | HCID 67218699 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 11551917 | HCID 11551917 | — |
Reaction Steps
A solution of BEMP (90 μL, 0.31 mmol) in DMF (400 μL) is added to a solution of (2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester (40 mg, 0.20 mmol) in DMF (400 μL). After 40-50 minutes, a solution of 4-methyl-benzenesulfonyl chloride (60 mg, 0.31 mmol) in DMF (400 μL) is added. After a further 30 minutes, 1M aqueous NaOH (800 μL) is added, and the reaction is shaken mechanically for 105 minutes, then 1M aqueous HCl (800 μL) is added. The reaction is partitioned between water and CH2Cl2. The organic phase is loaded directly onto a pre-packed Isolute™ silica column and eluted with EtOAc to give crude product which is triturated with water to afford [2-methyl-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid; MH+=345.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08455645B2 |
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| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-58a44f637b414f4c867b19efe4db3886 |
|---|
| Source note | uspto-grants-2013_06 |
|---|
