Ethyl Acetate → HCID 67003447, compound

HRID 2362656Notes

Reaction equation

HRID 2362656 reaction equation
[Cl:1][C:2]1[C:3]([C:22]2[S:26][C:25]([C:27]3([O:31][CH2:32][O:33][CH3:34])[CH2:30][CH2:29][CH2:28]3)=[N:24][CH:23]=2)=[C:4]2[CH:10]=[C:9](I)[N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1.[C:35]([O:39][C:40]([N:42]1[CH2:51][CH2:50][C:49]2[C:44](=[CH:45][C:46](B(O)O)=[CH:47][CH:48]=2)[CH2:43]1)=[O:41])([CH3:38])([CH3:37])[CH3:36].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:1][C:2]1[C:3]([C:22]2[S:26][C:25]([C:27]3([O:31][CH2:32][O:33][CH3:34])[CH2:30][CH2:29][CH2:28]3)=[N:24][CH:23]=2)=[C:4]2[CH:10]=[C:9]([C:46]3[CH:45]=[C:44]4[C:49]([CH2:50][CH2:51][N:42]([C:40]([O:39][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:41])[CH2:43]4)=[CH:48][CH:47]=3)[N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 66897174HCID 66897174, compoundHCID 67003444HCID 67003444, compound

Product 1

HCID 67003447HCID 67003447, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A stirring solution of Example 1F (0.1 g, 0.159 mmol) and 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-7-ylboronic acid (0.053 g, 0.191 mmol) in N,N-dimethylformamide (1.4 mL) was treated with saturated aqueous sodium bicarbonate (0.35 mL) followed by bis(triphenylphosphine)palladium(II) chloride (0.008 g, 0.012 mmol). The suspension was heated at 65° C. for 4 hours. The reaction was cooled to ambient temperature, and ethyl acetate and water were added. The layers were separated, and the aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The concentrate was purified by flash chromatography on silica gel, eluting with a gradient of from 0% to 25% ethyl acetate in hexane, to provide the title compound. MS ESI(+) m/z 735.2 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with additional ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash chromatography on silica gel
  9. washeluting with a gradient of from 0% to 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d7c6e2e4a85b43b5bbd50fc0ea9b425a
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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