Toluene → HCID 46214203, compound

HRID 1422497Notes

Reaction equation

HRID 1422497 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[C:5]2[N:18]=[CH:19][N:20]([CH:21]([CH3:23])[CH3:22])[C:4]=2[CH:3]=1.[F:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[N:29][CH:30]=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.O.C(O)C>[F:24][C:25]1[CH:26]=[C:27]([C:2]2[N:7]=[C:6]([NH:8][CH2:9][CH2:10][C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[C:5]3[N:18]=[CH:19][N:20]([CH:21]([CH3:23])[CH3:22])[C:4]=3[CH:3]=2)[CH:28]=[N:29][CH:30]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 86643468HCID 86643468, compound

Product 1

HCID 46214203HCID 46214203, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A 5 ml microwave reaction vial was charged with 4-(2-(6-chloro-1-isopropyl-1H-imidazo[4,5-c]pyridin-4-ylamino)ethyl)phenol (c): (17 mg, 0.051 mmol), 5-fluoropyridin-3-ylboronic acid (72 mg, 0.51 mmol), and tetrakis(triphenylphosphine)palladium(0) (36 mg, 0.031 mmol). To this mixture was added toluene (1 ml), ethanol (0.5 ml) and aqueous sodium carbonate solution (2M, 0.5 ml). The vial was sealed and the reaction mixture was stirred at 140° C. under microwave irradiation for 2 hours. Water was added to the cooled mixture, which was extracted with ethyl acetate (5 ml×3). The organic fractions were combined, dried over sodium sulfate, and concentrated. The residue was purified by reverse-phase HPLC (C18 column, eluting with ACN—H2O 0.05% TFA) to afford the title compound as an off-white solid.

Workup

  1. customA 5 ml microwave reaction
  2. customThe vial was sealed
  3. extractionwas extracted with ethyl acetate (5 ml×3)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by reverse-phase HPLC (C18 column, eluting with ACN—H2O 0.05% TFA)

Sources & evidence

ORD record
ord-1cdfd1356f5f41b69f04490e3e1fcfce
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

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