Toluene → HCID 22147975, compound

HRID 1823967Notes

Reaction equation

HRID 1823967 reaction equation
[CH3:1][N:2]([CH3:12])[S:3]([N:6]1[CH:10]=[C:9](Br)[N:8]=[CH:7]1)(=[O:5])=[O:4].[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:1][N:2]([CH3:12])[S:3]([N:6]1[CH:10]=[C:9]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)[N:8]=[CH:7]1)(=[O:5])=[O:4]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 221479874-Bromo-N,N-dimethyl-1H-imidazole-1-sulfonamide

Product 1

HCID 22147975HCID 22147975, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of the bromide from Step 1 (0.543 g), 4-fluorophenylboronic acid (0.31 g), tetrakis(triphenylphosphine) palladium (0) (0.2 g), 2M aqueous sodium carbonate (2.2 mL) and toluene (10 mL) was refluxed under N2 for 1.5 hours. The mixture was cooled, poured into water (75 mL) and extracted with ethyl actetate (2×25 mL). The extracts were dried over Na2SO4, filtered and concentrated. Flash column chromatography, eluting with 40% ethyl acetate-isohexane, gave 1-(dimethylaminosulfonyl)-4-(4-fluorophenyl)imidazole (0.417 g, 72%) as a yellow solid. MS (ES+) 270 ([MH]+).

Workup

  1. temperaturewas refluxed under N2 for 1.5 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl actetate (2×25 mL)
  4. dry with materialThe extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washFlash column chromatography, eluting with 40% ethyl acetate-isohexane

Sources & evidence

ORD record
ord-a4145a78ff794ec6b59c21d8583de54f
Source dataset
uspto-grants-2006_05
Patent number
US07041689B2

Reaction notes

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