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

HRID 1515679노트

반응식

HRID 1515679 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b63415e6a45540c3aa627361abe520c8
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222416B2

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