Sodium Bicarbonate → HCID 25003296, compound

HRID 2176861Notes

Reaction equation

HRID 2176861 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])[C:10]=2[CH3:16])[CH:5]=[CH:4][C:3]=1B(O)O.C([O-])(O)=O.[Na+].Br[C:26]1[CH:31]=[CH:30][N:29]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:28](=[O:36])[C:27]=1[C:37]#[N:38]>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>[CH:33]1([CH2:32][N:29]2[CH:30]=[CH:31][C:26]([C:3]3[CH:4]=[CH:5][C:6]([O:8][C:9]4[CH:14]=[CH:13][N:12]=[C:11]([CH3:15])[C:10]=4[CH3:16])=[CH:7][C:2]=3[F:1])=[C:27]([C:37]#[N:38])[C:28]2=[O:36])[CH2:34][CH2:35]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 59234229HCID 59234229, compoundHCID 59287326HCID 59287326, compound

Product 1

HCID 25003296HCID 25003296, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of intermediate 22 (0.34 g 1.321 mmol) in 1,4-dioxane (5.5 ml) and a saturated solution of NaHCO3 (5.5 ml) was added intermediate 5 (0.28 g, 1.123 mmol). The resulting solution was degassed using a stream of nitrogen and to this was added Pd(PPh3)4 (0.15 mg, 0.132 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. The filtrate was diluted with EtOAc, and then it 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/AcOEt 1:1 as eluent). The desired fractions were collected and evaporated in vacuo to give a residue that was triturated with Et2O to yield compound 10 (0.068 g, 16%)

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. additionThe filtrate was diluted with EtOAc
  7. washit was washed with water
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe crude reaction mixture
  11. customwas then purified by column chromatography (silica gel; DCM to DCM/AcOEt 1:1 as eluent)
  12. customThe desired fractions were collected
  13. customevaporated in vacuo
  14. customto give a residue that
  15. customwas triturated with Et2O

Sources & evidence

ORD record
ord-c6744a3b66014b98b70e767b4108f3a3
Source dataset
uspto-grants-2015_06
Patent number
US09067891B2

Reaction notes

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