Potassium Carbonate → HCID 78210229, compound

HRID 2207013Notes

Reaction equation

HRID 2207013 reaction equation
Br[C:2]1[N:6]=[CH:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])=[CH:9][CH:8]=2)[N:3]=1.CC1(C)C(C)(C)OB([C:29]2[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=2)O1.C([O-])([O-])=O.[K+].[K+]>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.COCCOC.O>[F:19][C:14]([F:20])([O:13][C:10]1[CH:11]=[CH:12][C:7]([N:4]2[CH:5]=[N:6][C:2]([C:29]3[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=3)=[N:3]2)=[CH:8][CH:9]=1)[C:15]([F:18])([F:17])[F:16]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 893818873-bromo-1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazole

Product 1

HCID 78210229HCID 78210229, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

3-Bromo-1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazole (1.5 g, 4.2 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.12 g, 5.12 mmol), Pd(PPh3)4 (0.49 g, 0.424 mmol) and K2CO3 (1.17 g, 8.52 mmol) were combined in a round bottom flask in 5:1 DME/water (22 mL), and the solution was degassed with nitrogen for 15 min. The reaction was then heated for 18 h at 120° C. The reaction mixture was cooled and diluted with EtOAc and water. The layers were separated and the aqueous layer was extracted with EtOAc (2×50 ml). The combined organic extracts were dried over anhydrous MgSO4 and concentrated onto 8 g of Celite®. The Celite® was loaded onto a silica column and the target molecule was eluted using 0-100% EtOAc/hexanes to afford the title compound as a tan solid (1.13 g, 68%): 1H NMR (400 MHz, CDCl3) δ 8.52 (s, 1H), 7.99 (d, J=8.7 Hz, 2H), 7.78 (d, J=9.1 Hz, 2H), 7.36 (d, J=9.1 Hz, 2H), 6.76 (d, J=8.7 Hz, 2H), 3.90 (s, 2H); ESIMS m/z 371.2 ([M+H]+).

Workup

  1. customthe solution was degassed with nitrogen for 15 min
  2. temperatureThe reaction mixture was cooled
  3. additiondiluted with EtOAc and water
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (2×50 ml)
  6. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
  7. concentrationconcentrated onto 8 g of Celite®
  8. washthe target molecule was eluted

Sources & evidence

ORD record
ord-d2106a6ebc07456085b51e5dd98b9688
Source dataset
uspto-grants-2016_06
Patent number
US09376401B2

Reaction notes

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