Ethanol → HCID 25128268, compound

HRID 2240979Notes

Reaction equation

HRID 2240979 reaction equation
[NH2:1][C:2]1[N:3]([CH3:25])[C:4](=[O:24])[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19](Br)[CH:18]=2)([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH:14]([F:16])[F:15])=[CH:9][CH:8]=2)[N:6]=1.[CH:26]1(B2OC(C)(C)C(C)(C)O2)[CH2:28][CH2:27]1.CCO.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].COCCOC.O>[NH2:1][C:2]1[N:3]([CH3:25])[C:4](=[O:24])[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH:26]3[CH2:28][CH2:27]3)[CH:18]=2)([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH:14]([F:16])[F:15])=[CH:9][CH:8]=2)[N:6]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27580152-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 597903072-amino-4-(3-bromophenyl)-4-(4-(difluoromethoxy)phenyl)-1-methyl-1H-imidazol-5(4H)-one

Product 1

HCID 25128268HCID 25128268, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
165 °C

Procedure

To a microwave vessel containing 2-amino-4-(3-bromophenyl)-4-(4-(difluoromethoxy)phenyl)-1-methyl-1H-imidazol-5(4H)-one (103 mg, 0.25 mmol) and cyclopropylboronic acid pinacol ester (84 mg, 0.5 mmol) in 4 ml of 1:1:3 ratio of EtOH:water:1,2-dimethoxyethane, palladium(0) teterakis and aqueous sodium carbonate (400 μL of 2N solution) were added. The reaction mixture was heated in CEM microwave at 165° C. (40 mW power) for 8 minutes. The reaction mixture was filtered, and partitioned between DCM and water. The water layer was extracted w/DCM and the combined organic layer was dried (MgSO4) and concentrated under reduced pressure to afford crude product which was purified by reverse chromatography ((M+H)+ 372.4).

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompartitioned between DCM and water
  3. extractionThe water layer was extracted w/DCM
  4. dry with materialthe combined organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto afford crude product which
  7. customwas purified by reverse chromatography ((M+H)+ 372.4)

Sources & evidence

ORD record
ord-3c0d00a1705f481cbe15007a4051960a
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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