5-chloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one → 5-Chloro-2,3-dihydro-1H-pyrrolo[3,2-B]pyridine

HRID 448589Notes

Reaction equation

HRID 448589 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH2:8][C:9](=O)[NH:10][C:5]2=[CH:4][CH:3]=1>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][NH:10][C:5]2=[CH:4][CH:3]=1

Participants

3

Conditions

Temperature
60 °C

Procedure

5-Chloro-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one (78 mg, 0.46 mmol) was dissolved in THF (1.5 mL). BH3 (1M in THF, 0.92 mL, 0.92 mmol) was added and the mixture was stirred at 60° C. for 3 h. The mixture was cooled to room temperature, diluted with THF and quenched with 1N HCl. The mixture was treated with 2N NaOH until basic and was extracted with ether. The organic extracts were dried, filtered and evaporated to afford 20a.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched with 1N HCl
  3. additionThe mixture was treated with 2N NaOH until basic and
  4. extractionwas extracted with ether
  5. customThe organic extracts were dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c55c26ce67d4440397614d5737f82358
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Reaction notes

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