1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 46179269, compound

HRID 2088417Notes

Reaction equation

HRID 2088417 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[N:8][N:7]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]4[N:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)=[CH:19][N:18]=4)[CH:12]=3)[C:6]=2[CH:32]=1.[CH3:33][N:34]1[CH:38]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH:36]=[N:35]1.O.O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:33][N:34]1[CH:38]=[C:37]([C:2]2[CH:3]=[CH:4][C:5]3[N:9]=[N:8][N:7]([CH2:10][C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([C:17]5[N:18]=[CH:19][C:20]([O:23][CH2:24][CH2:25][N:26]6[CH2:31][CH2:30][O:29][CH2:28][CH2:27]6)=[CH:21][N:22]=5)[CH:12]=4)[C:6]=3[CH:32]=2)[CH:36]=[N:35]1

Participants

6

Reactant 3

HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 18407952Tripotassium phosphate trihydrateHCID 58289712HCID 58289712, compound

Product 1

HCID 46179269HCID 46179269, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

200 mg (0.352 mmol) of 6-bromo-1-{3-[5-(2-morpholin-4-ylethoxy)pyrimidin-2-yl]benzyl}-1H-benzotriazole, 80.6 mg (0.387 mmol) of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 150 mg (0.704 mmol) of tripotassium phosphate trihydrate are suspended in 6 ml of ethylene glycol dimethyl ether, degassed evacuated and flushed with nitrogen a number of times. 24.7 mg (0.035 mmol) of bis(triphenylphosphine)palladium(II) chloride are added, and the mixture is again evacuated and flushed with nitrogen. The reaction mixture is stirred at 80° C. for 24 h. Water is added to the reaction mixture, which is then rendered basic using 32% NaOH and extracted with DCM. The organic phase is dried over sodium sulfate, evaporated under reduced pressure in a rotary evaporator and purified by column chromatography on silica gel; yield: 41 mg, HPLC: Rt=2.08 min (method C), LC-MS: [M+H]+=497;

Workup

  1. customdegassed
  2. customevacuated
  3. customflushed with nitrogen a number of times
  4. customthe mixture is again evacuated
  5. customflushed with nitrogen
  6. additionWater is added to the reaction mixture, which
  7. extractionextracted with DCM
  8. dry with materialThe organic phase is dried over sodium sulfate
  9. customevaporated under reduced pressure in a rotary evaporator
  10. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6cd270f0bd0d4957af17d60cb604629a
Source dataset
uspto-grants-2013_05
Patent number
US08435986B2

Reaction notes

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