Sodium Carbonate → HCID 25004351, compound

HRID 2401683Notes

Reaction equation

HRID 2401683 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13](B2OC(C)(C)C(C)(C)O2)[CH:12]=[CH:11][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.C([O-])([O-])=O.[Na+].[Na+].Br[C:31]1[CH:36]=[CH:35][N:34]([CH2:37][CH2:38][CH:39]2[CH2:41][CH2:40]2)[C:33](=[O:42])[C:32]=1[C:43]#[N:44]>O1CCOCC1.CCOC(C)=O.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>[Cl:1][C:2]1[CH:14]=[C:13]([C:31]2[CH:36]=[CH:35][N:34]([CH2:37][CH2:38][CH:39]3[CH2:41][CH2:40]3)[C:33](=[O:42])[C:32]=2[C:43]#[N:44])[CH:12]=[CH:11][C:3]=1[O:4][CH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 59272906HCID 59272906, compoundHCID 59272907HCID 59272907, compound

Product 1

HCID 25004351HCID 25004351, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of intermediate 18 (0.57 g, 1.7 mmol) in 1,4-dioxane (2 ml) and a saturated solution of Na2CO3 (2 ml) was added intermediate 9 (0.45 g, 1.7 mmol). The resulting solution was degassed using a stream of nitrogen and to this was added Pd(PPh3)4 (0.19 mg, 0.17 mmol). The reaction was then microwaved in a sealed tube at 150° C. for 10 minutes. The resulting cooled reaction mixture was then diluted with EtOAc and filtered through a pad of diatomaceous earth. The filtrate was washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude reaction mixture was then purified by column chromatography (silica gel; DCM to DCM/EtOAc up to 30% as eluent). The desired fractions were collected and evaporated in vacuo to yield compound 4 (0.108 g, 17%).

Workup

  1. customThe resulting solution was degassed
  2. customThe reaction was then microwaved in a sealed tube at 150° C. for 10 minutes
  3. temperatureThe resulting cooled
  4. customreaction mixture
  5. filtrationfiltered through a pad of diatomaceous earth
  6. washThe filtrate was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe crude reaction mixture
  10. customwas then purified by column chromatography (silica gel; DCM to DCM/EtOAc up to 30% as eluent)
  11. customThe desired fractions were collected
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-c483db772d774c709e09f0c1dc83d9d9
Source dataset
uspto-grants-2014_08
Patent number
US08796311B2

Reaction notes

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