Water → HCID 13875439, compound

HRID 2278595Notes

Reaction equation

HRID 2278595 reaction equation
C([BH3-])#N.[Na+].[CH3:5][C:6]1[C:14]2[C:13]([OH:15])=[CH:12][CH:11]=[CH:10][C:9]=2[NH:8][CH:7]=1.O>C(O)(=O)C>[OH:15][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[CH:6]([CH3:5])[CH2:7][NH:8]2

Participants

5

Reactant 3

HCID 962WaterHCID 5897743-Methyl-1H-indol-4-olHCID 5003444Sodium cyanoborohydride

Product 1

HCID 13875439HCID 13875439, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

1.35 g of sodium cyanoborohydride are gradually added to a solution of 1.0 g of 3-methyl-1H-indol-4-ol in 35 ml of acetic acid under argon cooled to a temperature of about 15° C. The reaction mixture is allowed to warm up to ambient temperature. After 16.5 hours, the reaction mixture is treated with 15 ml of water, and then concentrated to dryness under reduced pressure. The residue is taken up in 75 ml of ethyl acetate, and then treated with 60 ml of a saturated sodium hydrogen carbonate solution. After stirring for 1 hour and then settling out, the organic phase is separated and the aqueous phase is extracted with 50 ml of ethyl acetate. The organic phases are combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and then concentrated to dryness under reduced pressure. The residue is purified by chromatography on a 70 g cartridge of 15-40 μm silica, elution being carried out with an 80/20 v/v cyclohexane/ethyl acetate mixture, with a flow rate of 80 ml/min. 0.45 g of 4-hydroxy-3-methylindoline is thus obtained in the form of a pale yellow solid, the characteristics of which are the following:

Workup

  1. temperatureto warm up to ambient temperature
  2. concentrationconcentrated to dryness under reduced pressure
  3. additiontreated with 60 ml of a saturated sodium hydrogen carbonate solution
  4. customthe organic phase is separated
  5. extractionthe aqueous phase is extracted with 50 ml of ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure
  10. customThe residue is purified by chromatography on a 70 g cartridge of 15-40 μm silica, elution

Sources & evidence

ORD record
ord-55ab8fdb06d849dfa81946d22ed7c450
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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