1,4-Dioxane → HCID 21841477, compound

HRID 400250Notes

Reaction equation

HRID 400250 reaction equation
[CH:1]([N:4]([CH:15]([CH3:17])[CH3:16])[C:5](=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1)([CH3:3])[CH3:2].B(O)O.[Br-].[K+].[O:23]1[CH2:28][CH2:27]OCC1>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>[CH:1]([N:4]([CH:15]([CH3:17])[CH3:16])[C:5](=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:7]2[CH:8]=[CH:9][C:27]([CH:28]=[O:23])=[CH:5][CH:6]=2)=[CH:9][CH:8]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 61668Boronic AcidHCID 253877Potassium BromideHCID 21841495HCID 21841495, compound

Product 1

HCID 21841477HCID 21841477, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of 3 g of the product of Stage A, 1.66 g of boronic acid (Preparation 5), 3.5 g of monohydrated potassium phosphate, 1.32 g of potassium bromide and 300 mg of Pd(PPh3)4 (palladium tetrakis) in 50 ml of dioxane was refluxed for 12 hours. After pouring the reaction medium into a water-ice mixture, and carrying out extraction with ethyl acetate, the organic phase was dried, filtered and evaporated under reduced pressure. The crude product was purified by chromatography, eluting with a cyclohexane/ethyl acetate mixture (85/15) to obtain 1.95 g of the expected product with a Rf=0.05 (cyclohexane/ethyl acetate 85/15).

Workup

  1. temperaturewas refluxed for 12 hours
  2. extractionextraction with ethyl acetate
  3. customthe organic phase was dried
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by chromatography
  7. washeluting with a cyclohexane/ethyl acetate mixture (85/15)

Sources & evidence

ORD record
ord-dfd394d5458c48b9b266d113607b4bf0
Source dataset
uspto-grants-1998_10
Patent number
US05827887

Reaction notes

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