Diisobutylaluminumhydride → (1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-methanol

HRID 1515679Notes

Reaction equation

HRID 1515679 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:13]=[CH:12][N:11]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])[C:8]2=[N:9][CH:10]=1)=O.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[C:17]1([S:14]([N:11]2[C:8]3=[N:9][CH:10]=[C:5]([CH2:3][OH:2])[CH:6]=[C:7]3[CH:13]=[CH:12]2)(=[O:15])=[O:16])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 42609297methyl 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

Product 1

HCID 67229270(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-methanolYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester (prepared as in Example 1, 8 g, 25.3 mmol) in dry tetrahydrofuran (100 mL) was added diisobutylaluminum hydride (126 mL, 126 mmol) at −78° C. The mixture was warmed to room temperature and stirred for 1 h. The mixture was cooled to 0° C. and quenched with a saturated aqueous potassium sodium tartrate solution, and then stirred for 30 min. The resulting mixture was filtered, washed with tetrahydrofuran (300 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford (1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-methanol (6.5 g, 89.2%) as a light yellow solid: LC/MS m/e calcd for C14H12N2O3S [M+H]+ 289.33, observed 289.1.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customquenched with a saturated aqueous potassium sodium tartrate solution
  3. stirringstirred for 30 min
  4. filtrationThe resulting mixture was filtered
  5. washwashed with tetrahydrofuran (300 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b63415e6a45540c3aa627361abe520c8
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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