Sodium cyanoborohydride → HCID 66868381, compound

HRID 1909892Notes

Reaction equation

HRID 1909892 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=1)[NH:7][CH:6]=[CH:5]2.C([BH3-])#N.[Na+]>C(O)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=1)[NH:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 58125347HCID 58125347, compound

Product 1

HCID 66868381HCID 66868381, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of ethyl 5-chloro-1H-indole-7-carboxylate (3.0 g) and acetic acid (30 mL) was added sodium cyanoborohydride (2.5 g), followed by stirring at room temperature for 19 hours. The reaction mixture was concentrated under reduced pressure, and the residue was adjusted to pH 8 by adding saturated aqueous sodium bicarbonate. After extraction with chloroform, the organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was added with diethyl ether/hexane (1/5), solidified, and collected by filtration. To this solid was added ethyl acetate (10 mL), and 4 M hydrogen chloride ethyl acetate (10 mL) was added thereto, followed by concentration under reduced pressure. To the residue was added diethyl ether/hexane mixture (1/5), and the solid was collected by filtration and dried under reduced pressure to obtain ethyl 5-chloroindoline-7-carboxylate hydrochloride (1.6 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionby adding saturated aqueous sodium bicarbonate
  3. extractionAfter extraction with chloroform
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. additionThe residue was added with diethyl ether/hexane (1/5)
  8. filtrationsolidified, and collected by filtration
  9. additionTo this solid was added ethyl acetate (10 mL), and 4 M hydrogen chloride ethyl acetate (10 mL)
  10. additionwas added
  11. concentrationfollowed by concentration under reduced pressure
  12. additionTo the residue was added diethyl ether/hexane mixture (1/5)
  13. filtrationthe solid was collected by filtration
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-16540932560c4df7803c61d7e3397afe
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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