1,2-Dimethoxyethane → HCID 68720623, compound

HRID 885115Notes

Reaction equation

HRID 885115 reaction equation
I[C:2]1[S:6][C:5]([C:7]2([O:11][CH2:12][C:13]([O:15][CH2:16]C)=[O:14])[CH2:10][CH2:9][CH2:8]2)=[N:4][CH:3]=1.[F-].[Cs+].CC1(C)C(C)(C)OB([C:28]2[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=2)O1.C(COC)OC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO>[NH2:32][C:31]1[CH:33]=[CH:34][C:28]([C:2]2[S:6][C:5]([C:7]3([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH2:8][CH2:9][CH2:10]3)=[N:4][CH:3]=2)=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 25953Cesium fluorideHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 68721618HCID 68721618, compound

Product 1

HCID 68720623HCID 68720623, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution of Example 24A (0.750 g, 2/04 mmol), CsF (0.930 g, 6.12 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.447 g, 2.04 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.231 g, 0.200 mmol) in a solvent mixture of dimethoxyethane (5 mL) and methanol (5 mL) was heated to 90° C. for 16 h. The reaction was cooled to room temperature and partitioned between H2O (10 mL) and ethyl acetate (10 mL). The layers were separated, and the aqueous was extracted with additional ethyl acetate (2×10 mL). The combined organics were dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on SiO2 gel, eluting with a gradient of 10% ethyl acetate in hexane to 50% ethylacetate in hexane, to give the title compound. MS (ESI) m/z 319 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. custompartitioned between H2O (10 mL) and ethyl acetate (10 mL)
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with additional ethyl acetate (2×10 mL)
  5. dry with materialThe combined organics were dried with anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on SiO2 gel
  9. washeluting with a gradient of 10% ethyl acetate in hexane to 50% ethylacetate in hexane

Sources & evidence

ORD record
ord-393bdaa6e4e84442b484155fa6d5416a
Source dataset
uspto-grants-2012_08
Patent number
US08242139B2

Reaction notes

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