Sodium Carbonate → HCID 57581528, compound

HRID 1689948Notes

Reaction equation

HRID 1689948 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:14](C)[CH2:13]2)=[N:4][N:3]=1.[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:35](=O)([O-])[O-].[Na+].[Na+].C([O-])([O-])=O.[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:35][C@H:13]1[N:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:3][N:4]=2)[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:14]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 86627844HCID 86627844, compound

Product 1

HCID 57581528HCID 57581528, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

(R)-tert-butyl 4-(4-chlorophthalazin-1-yl)-2-methylpiperazine-1-carboxylate (0.500 g, 1.38 mmol), phenylboronic acid (0.168 g, 1.38 mmol), and tetrakis(triphenylphosphine)palladium (0) (79.9 mg, 0.069 mmol) were placed in a flask under argon. Degassed toluene (15 mL) and aqueous sodium carbonate (2.0 M, 1.5 mL) were added and the reaction heated at 100° C. for 22 hours. The reaction was allowed to cool before being added to 80 mL aqueous K2CO3 (10%). The aqueous phase was extracted with dichloromethane three times, and the combined organics were dried (MgSO4) and evaporated to give a yellow oil. Chromatography over silica gel with a gradient of hexanes/0-70% ethyl acetate gave an off-white solid. 1H-NMR (500 Mhz) δ 1.17 (br d, J=5.5 Hz, 3H), 1.44 (s, 9H), 3.40-3.65 (series of m, 5H), 3.82 (m, 1H), 4.06 (m, 1H), 7.47 (m, 3H), 7.69 (m, 3H), 7.78 (td, J=6.7, 1.2 Hz, 1H), 7.97 (d, J=7.9 Hz, 1H), 8.09 (d, J=8.5 Hz, 1H).

Workup

  1. temperatureto cool
  2. extractionThe aqueous phase was extracted with dichloromethane three times
  3. dry with materialthe combined organics were dried (MgSO4)
  4. customevaporated
  5. customto give a yellow oil

Sources & evidence

ORD record
ord-ab1fc0a734704fc397d671b43850c632
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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