Cesium carbonate → HCID 86691857, compound

HRID 1616243Notes

Reaction equation

HRID 1616243 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH2:17][CH:18]=[CH2:19])[C:9](=[O:16])[N:10]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:5]2=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([OH:36])([CH3:35])[CH3:34])=[CH:29][C:28]=1B1OC(C)(C)C(C)(C)O1>C(P([Pd]P(C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C)(C)C.CN1C(=O)CCC1>[CH3:13][C:12]([CH3:15])([CH3:14])[CH2:11][N:10]1[C:5]2[C:6](=[N:7][C:2]([C:32]3[CH:31]=[C:30]([C:33]([OH:36])([CH3:34])[CH3:35])[CH:29]=[CH:28][C:27]=3[CH3:26])=[CH:3][CH:4]=2)[N:8]([CH2:17][CH:18]=[CH2:19])[C:9]1=[O:16]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 674666895-(2-Hydroxy-2-propyl)-2-methylphenylboronic Acid Pinacol EsterHCID 86691856HCID 86691856, compound

Product 1

HCID 86691857HCID 86691857, compound

Reagents, catalysts & solvents 2

HCID 178454917HCID 178454917, compoundCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

5-Chloro-1-(2,2-dimethylpropyl)-3-(prop-2-en-1-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (71-5, 100 mg, 0.36 mmol, 1.0 equiv), Cs2CO3 (1.17 g, 3.57 mmol, 10.0 equiv), 2-[4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propan-2-ol (225 mg, 0.82 mmol, 2.3 equiv), and bis(tri-t-butyl-phosphino)palladium (18.3 mg, 0.04 mmol, 0.1 equiv) were added to anhydrous NMP (4 mL). The resulting suspension was warmed to 100° C. for 20 min in a microwave emitter. Following this duration, the reaction contents were filtered through Celite® and washed with EtOAc (5 mL). The filtrate was then diluted with saturated aqueous NaHCO3 (5 mL). The layers were separated and the aqueous layer was back-extracted with 3×5 mL EtOAc. The combined organics were dried over Na2SO4, filtered and concentrated to give a brown semi-solid. Purification by reverse-phase HPLC afforded 1-(2,2-dimethylpropyl)-5-[5-(1-hydroxy-1-methylethyl)-2-methylphenyl]-3-prop-2-en-1-yl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (71-6) as a white solid. HRMS (M+H)+: observed=394.2490, calculated=394.2489.

Workup

  1. customthe reaction contents
  2. filtrationwere filtered through Celite®
  3. washwashed with EtOAc (5 mL)
  4. additionThe filtrate was then diluted with saturated aqueous NaHCO3 (5 mL)
  5. customThe layers were separated
  6. extractionthe aqueous layer was back-extracted with 3×5 mL EtOAc
  7. dry with materialThe combined organics were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a brown semi-solid
  11. customPurification by reverse-phase HPLC

Sources & evidence

ORD record
ord-b98782f2ea05480ca487661767f65a65
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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