Sodium Bicarbonate → HCID 25002942, compound

HRID 2176857Notes

Reaction equation

HRID 2176857 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])[N:9]=[C:8]([CH3:13])[CH:7]=1.C([O-])(O)=O.[Na+].Br[C:32]1[CH:37]=[CH:36][N:35]([CH2:38][CH2:39][CH2:40][CH3:41])[C:34](=[O:42])[C:33]=1[C:43]#[N:44]>O1CCOCC1.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>[CH2:38]([N:35]1[CH:36]=[CH:37][C:32]([C:16]2[CH:15]=[CH:14][C:4]([O:5][C:6]3[CH:7]=[C:8]([CH3:13])[N:9]=[C:10]([CH3:12])[CH:11]=3)=[CH:3][C:2]=2[F:1])=[C:33]([C:43]#[N:44])[C:34]1=[O:42])[CH2:39][CH2:40][CH3:41]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 59234241HCID 59234241, compoundHCID 59287324HCID 59287324, compound

Product 1

HCID 25002942HCID 25002942, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of intermediate 18 (1.078 mmol) in 1,4-dioxane (6 ml) and a saturated solution of NaHCO3 (5 ml) was added intermediate 6 (0.25 g, 0.979 mmol). The resulting solution was degassed using a stream of nitrogen and to this was added Pd(PPh3)4 (0.113 mg, 0.098 mmol). The reaction was then microwaved in a sealed tube at 150° C. for 10 minutes. The resulting cooled reaction mixture was filtered through a pad of diatomaceous earth and the pad of diatomaceous earth was washed with EtOAc. The combined filtrates were washed with water and the organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The crude reaction mixture was then purified by column chromatography (silica gel; DCM to DCM/MeOH up to 2% as eluent). The desired fractions were collected and evaporated in vacuo to yield compound 6 that was precipitated from diethylether (0.220 g, 57%).

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. filtrationwas filtered through a pad of diatomaceous earth
  6. washthe pad of diatomaceous earth was washed with EtOAc
  7. washThe combined filtrates were washed with water
  8. customthe organic layer was separated
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo
  11. customThe crude reaction mixture
  12. customwas then purified by column chromatography (silica gel; DCM to DCM/MeOH up to 2% as eluent)
  13. customThe desired fractions were collected
  14. customevaporated in vacuo

Sources & evidence

ORD record
ord-3c87a01fe3e549c49feba32927ea9fe3
Source dataset
uspto-grants-2015_06
Patent number
US09067891B2

Reaction notes

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