Hydrochloric Acid → HCID 86713228, compound

HRID 1056825Notes

Reaction equation

HRID 1056825 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([CH:10]=[CH:11][C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[B]=O.[CH3:20][O:21][C:22]1[CH:29]=[C:28]([O:30][CH2:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[CH:27]=[CH:26][C:23]=1[CH:24]=O.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:1]1[C:9]2[C:4](=[C:5](/[CH:10]=[CH:11]/[C:12](=[O:17])[CH2:13][C:14](=[O:16])/[CH:15]=[CH:24]/[C:23]3[CH:26]=[CH:27][C:28]([O:30][CH2:31][C:32]4[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=4)=[CH:29][C:22]=3[O:21][CH3:20])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 21531Triisopropyl borateHCID 516892Sodium BicarbonateHCID 6327189Boron monoxideHCID 86713229HCID 86713229, compoundHCID 86713230HCID 86713230, compound

Product 1

HCID 86713228HCID 86713228, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
70 °C

Procedure

In a 20 mL reaction vessel were placed 31.0 mg (136 μmol) of 6-(1H-indol-4-yl)hex-5-ene-2,4-dione and 13.2 mg (0.190 mmol) of boron oxide and they were dissolved in 0.88 mL of ethyl acetate. To the mixture under stirring at 70° C., 33 mg (0.14 mmol) of 2-methoxy-4-(3-pyridylmethoxy)benzaldehyde and 62 μL (0.27 mmol) of triisopropyl borate were sequentially added. After the mixture was stirred at the same temperature for 1 hour, a solution of 2.7 μL (27 μmol) of piperidine in ethyl acetate (0.135 mL) was added and the mixture was further stirred for 1 hour. To the reaction mixture was added a 1:1 solution (0.4 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 42.8 mg (70% yield) of the title compound as an orange 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-a282338b6e4342d8a29043f01814b0a0
Source dataset
uspto-grants-2016_07
Patent number
US09399635B2

Reaction notes

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