Hydrochloric Acid → HCID 86713231, compound

HRID 1056826Notes

Reaction equation

HRID 1056826 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:6]=[CH:5][C:4]=1[CH:17]=[CH:18][C:19](=[O:24])[CH2:20][C:21](=[O:23])[CH3:22].[B]=O.[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][C:34]=2[CH:36]=O)[CH:29]=[CH:28]1.B(OC(C)C)(OC(C)C)OC(C)C.N1CCCCC1.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.[Cl-].[Na+].O>[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][C:34]=2/[CH:36]=[CH:22]/[C:21](=[O:23])[CH2:20][C:19](=[O:24])/[CH:18]=[CH:17]/[C:4]2[CH:5]=[CH:6][C:7]([O:9][CH2:10][C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)=[CH:8][C:3]=2[O:2][CH3:1])[CH:29]=[CH:28]1

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 21531Triisopropyl borateHCID 516892Sodium BicarbonateHCID 2734629Indole-7-carboxaldehydeHCID 6327189Boron monoxideHCID 86713232HCID 86713232, compound

Product 1

HCID 86713231HCID 86713231, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
70 °C

Procedure

In a 20 mL reaction vessel were placed 88 mg (0.27 mmol) of 6-[2-methoxy-4-(3-pyridylmethoxy)phenyl]hex-5-ene-2,4-dione and 26.4 mg (0.380 mmol) of boron oxide and they were dissolved in 1.76 mL of ethyl acetate. To the mixture under stirring at 70° C., 40 mg (0.27 mmol) of 1H-indole-7-carboxaldehyde and 124 μL (0.54 mmol) of triisopropyl borate were sequentially added. After the mixture was stirred at the same temperature for 1 hour, a solution of 5.4 μL (54 μmol) of piperidine in ethyl acetate (0.27 mL) was added and the mixture was further stirred for 1 hour. To the reaction mixture was added a 1:1 solution (0.8 mL) of 1 N hydrochloric acid and saturated brine at room temperature and the mixture was stirred for 5 minutes to 1 hour (further, the mixture was neutralized with a saturated sodium bicarbonate aqueous solution as needed). The resulting organic phase was directly subjected to purification by silica gel column chromatography (hexane/ethyl acetate or methylene chloride/methanol) to give 21.6 mg (18% yield) of the title compound as a yellow powder.

Workup

  1. customIn a 20 mL reaction vessel
  2. stirringAfter the mixture was stirred at the same temperature for 1 hour
  3. stirringthe mixture was further stirred for 1 hour
  4. stirringthe mixture was stirred for 5 minutes to 1 hour (further, the mixture
  5. customThe resulting organic phase was directly subjected to purification by silica gel column chromatography (hexane/ethyl acetate or methylene chloride/methanol)

Sources & evidence

ORD record
ord-ce2df1ebd6214485b8854ea27c7fc4e2
Source dataset
uspto-grants-2016_07
Patent number
US09399635B2

Reaction notes

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