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Sodium Carbonate → N-Cyclopropyl-2,6-bis[(1E)-3-methoxyprop-1-en-1-yl]isonicotinamide

HRID 561834
Notes
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Reaction equation

HRID 561834 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:11]=[C:12](Cl)[N:13]=1)[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[CH3:15][O:16][CH2:17]/[CH:18]=[CH:19]/B1OC(C)(C)C(C)(C)O1.[C:29]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:34]=CC=C[CH:30]=1.[C:48](=O)([O-])[O-:49].[Na+].[Na+]>CN(C=O)C.[Pd](Br)Br>[CH:8]1([NH:7][C:5](=[O:6])[C:4]2[CH:11]=[C:12](/[CH:30]=[CH:29]/[CH2:34][O:49][CH3:48])[N:13]=[C:2](/[CH:19]=[CH:18]/[CH2:17][O:16][CH3:15])[CH:3]=2)[CH2:10][CH2:9]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 162174432-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 215100262,6-Dichloro-N-cyclopropylisonicotinamide

Product 1

HCID 66761510N-Cyclopropyl-2,6-bis[(1E)-3-methoxyprop-1-en-1-yl]isonicotinamide

Reagents, catalysts & solvents 2

HCID 83469Palladium bromide (PdBr2)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2,6-dichloro-N-cyclopropylisonicotinamide from Amine 41, Step 1 (I eq.) in DMF (0.08 M) was added (2-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.7 eq.), palladium bromide (5% loading), triphenylphosphine (10% loading) and sodium carbonate (2 M aqueous solution, 5 eq.). The resulting suspension was heated at 100° C. for 8 h. The reaction mixture was quenched with water and extracted with ether. The combined organic extracts were washed with sat. aq. NaHCO3 and brine. Drying over Na2SO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a red oil. Purification by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc) afforded the title compound as a yellow oil.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ether
  3. washThe combined organic extracts were washed with sat. aq. NaHCO3 and brine
  4. dry with materialDrying over Na2SO4, filtration and concentration of the filtrate in vacuo
  5. customafforded the crude product as a red oil
  6. customPurification by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-577ce0bfa216420d91f2772d3771d42c
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063105B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes