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

HRID 561832
Notes
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Reaction equation

HRID 561832 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([O:14][CH3:15])[N:13]=1)[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[CH3:16][O:17][CH2:18]/[CH:19]=[CH:20]/B1OC(C)(C)C(C)(C)O1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.[Pd](Br)Br>[CH:8]1([NH:7][C:5](=[O:6])[C:4]2[CH:3]=[C:2](/[CH:20]=[CH:19]/[CH2:18][O:17][CH3:16])[N:13]=[C:12]([O:14][CH3:15])[CH:11]=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 845809352-Chloro-N-cyclopropyl-6-methoxyisonicotinamide

Product 1

HCID 66760917N-Cyclopropyl-2-methoxy-6-[(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-chloro-N-cyclopropyl-6-methoxyisonicotinamide from the previous step (1 eq.) in DMF (0.3 M) was added (2-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1 eq.), palladium bromide (5% loading), triphenylphosphine (10% loading) and sodium carbonate (2 M aqueous solution, 3 eq.). The resulting suspension was heated at 100° C. for 7 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 brown tar. Purification by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc) followed by recrystallization from Hex:ether afforded the title compound as a white solid.

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 brown tar
  6. customPurification by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc)
  7. customfollowed by recrystallization from Hex

Sources & evidence

ORD record
ord-b9f2faf003814cd486e079bdd716ec80
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