Sodium Carbonate → 3-(1-(2-Chlorophenyl)-1H-benzo[d][1,2,3]triazol-5-yl)-N-cyclopropyl-5-fluoro-4-methylbenzamide

HRID 1879448Notes

Reaction equation

HRID 1879448 reaction equation
[CH:1]1([NH:4][C:5](=[O:23])[C:6]2[CH:11]=[C:10](B3OC(C)(C)C(C)(C)O3)[C:9]([CH3:21])=[C:8]([F:22])[CH:7]=2)[CH2:3][CH2:2]1.Br[C:25]1[CH:40]=[CH:39][C:28]2[N:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:38])[N:30]=[N:31][C:27]=2[CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>O1CCOCC1.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>[Cl:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[N:29]1[C:28]2[CH:39]=[CH:40][C:25]([C:10]3[CH:11]=[C:6]([CH:7]=[C:8]([F:22])[C:9]=3[CH3:21])[C:5]([NH:4][CH:1]3[CH2:2][CH2:3]3)=[O:23])=[CH:26][C:27]=2[N:31]=[N:30]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 21914563N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 687701145-bromo-1-(2-chlorophenyl)-1H-benzo[d][1,2,3]triazole

Product 1

HCID 252345383-(1-(2-Chlorophenyl)-1H-benzo[d][1,2,3]triazol-5-yl)-N-cyclopropyl-5-fluoro-4-methylbenzamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
125 °C

Procedure

To a mixture of N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (100 mg, 0.31 mmol), 5-bromo-1-(2-chlorophenyl)-1H-benzo[d][1,2,3]triazole (110 mg, 0.34 mmol), tetrakis(triphenylphosphine)palladium(0) (18 mg, 0.016 mmol) in dioxane (3 mL) was added 1.3 mL of 2 N sodium carbonate solution. The reaction mixture was heated at 125° C. in a microwave for 30 min. The mixture was then treated with 2 mL of 1 N NaOH and extracted with 2×15 mL of EtOAc. The combined organic phase was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography on silical gel (30-70% of EtOAc in Hexanes) to give the title compound as an off white crystalline solid. MS (ESI, pos. ion) m/z: 421.0 (M+1).

Workup

  1. extractionextracted with 2×15 mL of EtOAc
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude material was purified by flash chromatography on silical gel (30-70% of EtOAc in Hexanes)

Sources & evidence

ORD record
ord-929ef3972a13410181088dc986c22196
Source dataset
uspto-grants-2012_11
Patent number
US08314131B2

Reaction notes

Loading…