Dichloromethane → 1-benzenesulfonyl-2-(2-cyclopentyl-acetyl)-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester

HRID 1515589Notes

Reaction equation

HRID 1515589 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:13]=[C:12]([CH:14]([OH:21])[CH2:15][CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[N:11]([S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:24])=[O:23])[C:8]2=[N:9][CH:10]=1)=[O:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.ClCCl>>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:13]=[C:12]([C:14](=[O:21])[CH2:15][CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[N:11]([S:22]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)(=[O:23])=[O:24])[C:8]2=[N:9][CH:10]=1)=[O:4]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 672279581-benzenesulfonyl-2-(2-cyclopentyl-1-hydroxy-ethyl)-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester

Product 1

HCID 672276051-benzenesulfonyl-2-(2-cyclopentyl-acetyl)-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl esterYield 93%

Conditions

Temperature
25 °C

Procedure

To a 25 mL round bottomed flask charged with 1-benzenesulfonyl-2-(2-cyclopentyl-1-hydroxy-ethyl)-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester (730 mg, 1.7 mmol) was added a solution of Dess-Martin periodinane in dichloromethane (0.3M, 12 mL, 3.6 mmol) at 25° C. The reaction mixture was stirred at 25° C. for 1 h and then quenched with a saturated aqueous sodium bicarbonate solution (10 mL). The mixture was extracted with ethyl acetate (100 mL), washed with a saturated aqueous sodium bicarbonate solution (3×20 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to give 1-benzenesulfonyl-2-(2-cyclopentyl-acetyl)-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester (670 mg, 93%) as a light yellow solid which was used without further purification: 1H NMR (400 MHz, CDCl3) δ ppm 1.26 (m, 2H), 1.52-1.74 (m, 4H), 1.97 (m, 2H), 2.45 (m, 1H), 3.04 (d, J=7.2 Hz, 2H), 3.98 (s, 3H), 6.99 (s, 1H), 7.57 (m, 2H), 7.65 (m, 1H), 8.43 (m, 2H), 8.55 (d, J=2.0 Hz, 1H), 9.21 (d, J=2.0 Hz, 1H).

Workup

  1. customquenched with a saturated aqueous sodium bicarbonate solution (10 mL)
  2. extractionThe mixture was extracted with ethyl acetate (100 mL)
  3. washwashed with a saturated aqueous sodium bicarbonate solution (3×20 mL), brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75f4dadcaa8747ebbdb4891d43f052b8
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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