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Potassium Carbonate → 4-Benzyloxy-3-cyclopropyl-1-cyclopropylmethyl-1H-pyridin-2-one

HRID 516630
Notes
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Reaction equation

HRID 516630 reaction equation
C([O-])(O)=O.[Na+].[CH:6]1(B(O)O)[CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+].[CH2:18]([O:25][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]=1I)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCOCC1>[CH2:18]([O:25][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[CH:6]1[CH2:8][CH2:7]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2760897Cyclopropylboronic acidHCID 594971024-Benzyloxy-1-cyclopropylmethyl-3-iodo-1H-pyridin-2-one

Product 1

HCID 594971164-Benzyloxy-3-cyclopropyl-1-cyclopropylmethyl-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Conditions

Temperature
175 °C

Procedure

NaHCO3 (1.0 g, excess), cyclopropylboronic acid (0.74 g, 8.93 mmol), potassium carbonate (1.23 g, 8.93 mmol) and [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium(II)-DCM complex (0.36 g, 0.45 mmol) were added to a solution of intermediate D10 (1.0 g, 2.98 mmol) in 1,4-dioxane (10 ml). The resulting mixture was heated at 175° C. for 20 minutes under microwave irradiation, after which it was filtered through diatomaceous earth and the solvent was evaporated in vacuo. The crude residue was purified by column chromatography (silica gel; 0-3% methanol/DCM as eluent). The desired fractions were collected and evaporated in vacuo yielding D34 (0.6 g, 69%).

Workup

  1. filtrationafter which it was filtered through diatomaceous earth
  2. customthe solvent was evaporated in vacuo
  3. customThe crude residue was purified by column chromatography (silica gel; 0-3% methanol/DCM as eluent)
  4. customThe desired fractions were collected
  5. customevaporated in vacuo
  6. customyielding D34 (0.6 g, 69%)

Sources & evidence

ORD record
ord-845de4cedd0046eaa462aadd49d1e39e
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09114138B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes