Cesium carbonate → 4-Phenyl-3-propyl-1H-isochromen-1-one

HRID 634403Notes

Reaction equation

HRID 634403 reaction equation
I[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[O:4][C:3]=1[CH2:13][CH2:14][CH3:15].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.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>[C:16]1([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:12])[O:4][C:3]=2[CH2:13][CH2:14][CH3:15])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 441304554-Iodo-3-propyl-1H-isochromen-1-one

Product 1

HCID 158933024-Phenyl-3-propyl-1H-isochromen-1-oneYield 16.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

4-Iodo-3-propyl-1H-isochromen-1-one (intermediate C20.2, 0.80 g, 2.55 mmol), phenylboronic acid (0.39 g, 3.18 mmol), Pd(PPh3)4 (0.15 g, 0.127 mmol) and Cs2CO3 (1.16 g, 3.57 mmol) were reacted in DMF (10 ml) at 80° C. for 3 hrs. The reaction was the partitioned between AcOEt and 1 M HClaqueous, washed with 1 M HClaqueous brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting crude was purified on a silica 500 Biotage cartridge eluting with a gradient of Hexane and AcOEt to give the title compound (0.11 g, 15.9%) as a yellowish oil.

Workup

  1. custompartitioned between AcOEt and 1 M HClaqueous
  2. washwashed with 1 M HClaqueous brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude was purified on a silica 500 Biotage cartridge
  6. washeluting with a gradient of Hexane and AcOEt

Sources & evidence

ORD record
ord-9ac87b0ec7a14e97aa81e4b17fba32d6
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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