Sodium Bicarbonate → HCID 25002590, compound

HRID 2176852Notes

Reaction equation

HRID 2176852 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1B1OC(C)(C)C(C)(C)O1)[O:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[N:7]=1.C([O-])(O)=O.[Na+].Br[C:32]1[CH:37]=[CH:36][N:35]([CH2:38][CH:39]2[CH2:41][CH2:40]2)[C:34](=[O:42])[C:33]=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>[CH:39]1([CH2:38][N:35]2[CH:36]=[CH:37][C:32]([C:16]3[CH:15]=[CH:14][C:4]([O:5][C:6]4[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[N:7]=4)=[CH:3][C:2]=3[F:1])=[C:33]([C:43]#[N:44])[C:34]2=[O:42])[CH2:40][CH2:41]1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 59234229HCID 59234229, compoundHCID 59287318HCID 59287318, compound

Product 1

HCID 25002590HCID 25002590, compound

Reagents, catalysts & solvents 3

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

Procedure

To a solution of intermediate 8 (1.42 mmol) in 1,4-dioxane (6 ml) and a saturated solution of NaHCO3 (5 ml) was added intermediate 5 (0.329 g, 1.3 mmol). The resulting solution was degassed using a stream of nitrogen and to this was added Pd(PPh3)4 (0.15 mg, 0.13 mmol). The reaction was then microwaved in a sealed tube at 140° C. for 5 minutes. The resulting cooled reaction mixture was then diluted with EtOAc and filtered through a pad of diatomaceous earth. The filtrate was washed with water, dried (Na2SO4) and concentrated in vacuo. The crude reaction mixture was then purified by column chromatography (silica gel; DCM to DCM/EtOAc up to 10% as eluent). The desired fractions were collected and evaporated in vacuo to yield compound 1 that was washed with diethyleter and dried in vacuum (0.207 g, 41%). Melting point: 137.0° C.

Workup

  1. customThe resulting solution was degassed
  2. customThe reaction was then microwaved in a sealed tube at 140° C. for 5 minutes
  3. temperatureThe resulting cooled
  4. customreaction mixture
  5. filtrationfiltered through a pad of diatomaceous earth
  6. washThe filtrate was washed with water
  7. dry with materialdried (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 10% as eluent)
  11. customThe desired fractions were collected
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-f579f45ad7cc4b35a604403e6bf390ea
Source dataset
uspto-grants-2015_06
Patent number
US09067891B2

Reaction notes

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