Sodium Bicarbonate → HCID 25002939, compound

HRID 2176855Notes

Reaction equation

HRID 2176855 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([CH3:15])[CH:10]=2)[CH:5]=[CH:4][C:3]=1B(O)O.C([O-])(O)=O.[Na+].Br[C:25]1[CH:30]=[CH:29][N:28]([CH2:31][CH2:32][CH2:33][CH3:34])[C:27](=[O:35])[C:26]=1[C:36]#[N:37]>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>[CH2:31]([N:28]1[CH:29]=[CH:30][C:25]([C:3]2[CH:4]=[CH:5][C:6]([O:8][C:9]3[CH:14]=[CH:13][N:12]=[C:11]([CH3:15])[CH:10]=3)=[CH:7][C:2]=2[F:1])=[C:26]([C:36]#[N:37])[C:27]1=[O:35])[CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 58103931HCID 58103931, compoundHCID 59234241HCID 59234241, compound

Product 1

HCID 25002939HCID 25002939, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of intermediate 14 (1.77 mmol) in 1,4-dioxane ml) and a saturated solution of NaHCO3 (6 ml) was added intermediate 6 (0.451 g, 1.77 mmol). The resulting solution was degassed using a stream of nitrogen and to this was added Pd(PPh3)4 (0.204 mg, 0.177 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 concentrated in vacuo. The crude reaction mixture was then purified by column chromatography (silica gel; DCM to DCM/MeOH up to 3% as eluent). The desired fractions were collected and evaporated in vacuo to yield compound 4 (0.45 g, 68%).

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. concentrationconcentrated in vacuo
  7. customThe crude reaction mixture
  8. customwas then purified by column chromatography (silica gel; DCM to DCM/MeOH up to 3% as eluent)
  9. customThe desired fractions were collected
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-31d5554fd8f04f6b8afd833002b490d9
Source dataset
uspto-grants-2015_06
Patent number
US09067891B2

Reaction notes

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