Cesium fluoride → HCID 68291014, compound

HRID 2205953Notes

Reaction equation

HRID 2205953 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)O1.Br[C:18]1[N:22]([CH3:23])[C:21]([CH3:24])=[N:20][CH:19]=1.[F-].[Cs+]>COCCOC.CO.CCOC(C)=O.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>[CH3:23][N:22]1[C:18]([C:9]2[CH:10]=[CH:11][C:12]([NH2:13])=[CH:14][CH:15]=2)=[CH:19][N:20]=[C:21]1[CH3:24]

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 72048795-bromo-1,2-dimethyl-1H-imidazole

Product 1

HCID 68291014HCID 68291014, compoundYield 56.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 86595564Dimethoxyethane methanolSolvent

Conditions

Temperature
150 °C

Procedure

Tetrakis(triphenylphosphine)palladium (0.053 g, 0.046 mmol) was added to a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.1 g, 0.456 mmol), 5-bromo-1,2-dimethyl-1H-imidazole (0.088 g, 0.502 mmol) and cesium fluoride (0.208 g, 1.369 mmol) in DME/MeOH (2/1, 2.9 mL). The reaction mixture was heated for 10 minutes at 150° C. under microwave irradiation. The reaction was diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude mixture was purified using Biotage silica gel column chromatography eluting with 1 to 5% MeOH/aq. NH3 (10/1) in DCM followed by filtration through a SCX-2 column to afford the title product as a white solid (48 mg, 56%). 1H NMR (500 MHz, CDCl3): δ 2.42 (s, 3H), 3.46 (s, 3H), 3.81 (br s, 2H), 6.71-6.74 (m, 1H), 6.85 (s, 1H), 7.12-7.14 (m, 1H).

Workup

  1. customquenched with water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude mixture was purified
  8. washeluting with 1 to 5% MeOH/aq
  9. filtrationNH3 (10/1) in DCM followed by filtration through a SCX-2 column

Sources & evidence

ORD record
ord-1fc3479359434fe89ebb1f0fd0763cd8
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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