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Sodium Carbonate → 1-(3-Methylbutyl)-4-[4-(tetrahydropyran-4-ylamino)-phenyl]-1H-pyridin-2-one

HRID 1024387
Notes
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Reaction equation

HRID 1024387 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[C:4](=[O:13])[CH:3]=1.[O:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21]2[CH:26]=[CH:25][C:24](B3OC(C)(C)C(C)(C)O3)=[CH:23][CH:22]=2)[CH2:16][CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+]>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>[CH3:11][CH:10]([CH3:12])[CH2:9][CH2:8][N:5]1[CH:6]=[CH:7][C:2]([C:24]2[CH:25]=[CH:26][C:21]([NH:20][CH:17]3[CH2:16][CH2:15][O:14][CH2:19][CH2:18]3)=[CH:22][CH:23]=2)=[CH:3][C:4]1=[O:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 594970904-Bromo-1-isopentylpyridin-2(1H)-oneHCID 59497754(Tetrahydropyran-4-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amine

Product 1

HCID 594977621-(3-Methylbutyl)-4-[4-(tetrahydropyran-4-ylamino)-phenyl]-1H-pyridin-2-oneYield 98.9%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of intermediate D4 (0.46 g, 1.9 mmol), intermediate D7 (0.69 g, 2.28 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.21 g, 0.19 mmol) in a mixture of dioxane (4 ml) and saturated aqueous sodium carbonate (4 ml) was heated at 150° C. for 10 minutes, under microwave irradiation. The crude was filtered over diatomaceous earth and washed with EtOAc. The organic layer was separated and washed with brine, dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; DCM/EtOAc 8:2 and finally EtOAc as eluent). The desired fractions were collected and evaporated in vacuo to yield D8 (0.64 g, 95%) as a yellow solid.

Workup

  1. filtrationThe crude was filtered over diatomaceous earth
  2. washwashed with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated in vacuo
  7. customThe crude product was purified by column chromatography (silica gel
  8. customThe desired fractions were collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-86e647a317b447fe85dda8e6466e5338
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722894B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes