Sodium Bicarbonate → HCID 25002937, compound

HRID 2176853Notes

Reaction equation

HRID 2176853 reaction equation
[F:1][C:2]1[CH:16]=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:14]=[CH:13][C:3]=1[O:4][C:5]1[C:6]([CH3:12])=[N:7][C:8]([CH3:11])=[CH:9][CH:10]=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:15]2[CH:14]=[CH:13][C:3]([O:4][C:5]3[C:6]([CH3:12])=[N:7][C:8]([CH3:11])=[CH:9][CH:10]=3)=[C:2]([F:1])[CH:16]=2)=[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 59287322HCID 59287322, compound

Product 1

HCID 25002937HCID 25002937, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of intermediate 12 (2 mmol) in 1,4-dioxane (6 ml) and a saturated solution of NaHCO3 (6 ml) was added intermediate 6 (0.51 g, 2 mmol). The resulting solution was degassed using a stream of nitrogen and to this was added Pd(PPh3)4 (0.231 mg, 0.2 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 2 (0.405 g, 52%).

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-f4ec938a3dbb41dcb41ee62ba741d210
Source dataset
uspto-grants-2015_06
Patent number
US09067891B2

Reaction notes

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