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

HRID 1515582Notes

Reaction equation

HRID 1515582 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:13]=[C:12]([CH:14]([OH:19])[CH2:15][CH:16]([CH3:18])[CH3:17])[N:11]([S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:22])=[O:21])[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:19])[CH2:15][CH:16]([CH3:18])[CH3:17])[N:11]([S:20]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)(=[O:21])=[O:22])[C:8]2=[N:9][CH:10]=1)=[O:4]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 672290341-benzenesulfonyl-2-(1-hydroxy-3-methyl-butyl)-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester

Product 1

HCID 672289171-benzenesulfonyl-2-(3-methyl-butyryl)-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl esterYield 66%

Conditions

Temperature
25 °C

Procedure

To a 25 ml, round bottomed flask charged with 1-benzenesulfonyl-2-(1-hydroxy-3-methyl-butyl)-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester (938 mg, 2.33 mmol) was added a solution of Dess-Martin periodinane in dichloromethane (0.3M, 15 mL, 4.5 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 (150 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-(3-methyl-butyryl)-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester (613 mg, 66%) as a light yellow solid which was used without further purification: LC/MS m/e calcd for C20H21N2O5S [M+H]+ 401.46, observed 401.3; 1H NMR (400 MHz, CDCl3) δ ppm 1.07 (d, J=6.6 Hz, 6H), 2.36 (m, 1H), 2.89 (d, J=7.0 Hz, 2H), 3.97 (s, 3H), 7.00 (s, 1H), 7.57 (brt, 2H), 7.64 (brt, 1H), 8.44 (br. d., 2H), 8.58 (d, J=2.0 Hz, 1H), 9.20 (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 (150 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-cd921d4486e641c9a72d6f682cca0ab3
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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