Toluene → HCID 67021739, compound

HRID 2094632Notes

Reaction equation

HRID 2094632 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH:13]3[CH2:14][O:15][CH2:16][CH:9]2[CH2:10][O:11][CH2:12]3)[N:5]=[C:4]([N:17]2[CH:22]3[CH2:23][O:24][CH2:25][CH:18]2[CH2:19][O:20][CH2:21]3)[N:3]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][CH:28]=1.C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>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.CCO>[CH:22]12[N:17]([C:4]3[N:5]=[C:6]([N:8]4[CH:13]5[CH2:14][O:15][CH2:16][CH:9]4[CH2:10][O:11][CH2:12]5)[N:7]=[C:2]([C:30]4[CH:31]=[CH:32][C:27]([NH2:26])=[CH:28][CH:29]=4)[N:3]=3)[CH:18]([CH2:25][O:24][CH2:23]1)[CH2:19][O:20][CH2:21]2

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 87239692HCID 87239692, compound

Product 1

HCID 67021739HCID 67021739, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

To a 10 mL vial were added 9,9′-(6-chloro-1,3,5-triazine-2,4-diyl)bis(3,7-dioxa-9-azabicyclo[3.3.1]nonane) (150 mg, 0.406 mmol), 4-aminophenylboronic acid pinacol ester (133 mg, 0.61 mmol), Pd(PPh3)4 (10 mg), toluene (1 mL), EtOH (1 mL) and 2M Na2CO3 aqueous solution (0.305 mL). The resulting mixture was heated at 120° C. for 20 minutes in microwave oven. The reaction mixture was cooled to room temperature. The aqueous phase was extracted with EtOAc, and the combined organic phases were dried over (MgSO4). The solvent was removed under reduced pressure and the residue was subjected to HPLC separation to give 4-(4,6-di(3,7-dioxa-9-azabicyclo[3.3.1]nonan-9-yl)-1,3,5-triazin-2-yl)aniline as a white solid (120 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe aqueous phase was extracted with EtOAc
  3. dry with materialthe combined organic phases were dried over (MgSO4)
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was subjected to HPLC separation

Sources & evidence

ORD record
ord-5e563a24584d4acf9a812cec8e0246bb
Source dataset
uspto-grants-2013_05
Patent number
US08445486B2

Reaction notes

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