Sodium Carbonate → HCID 59583401, compound

HRID 2170526Notes

Reaction equation

HRID 2170526 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]([CH3:14])=[C:12]([C:15]([OH:17])=[O:16])[N:11]=[N:10]2)=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]([CH3:14])=[C:12]([C:15]([OH:17])=[O:16])[N:11]=[N:10]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 27948281-[(4-Bromophenyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxylic acid

Product 1

HCID 59583401HCID 59583401, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 1-[(4-bromophenyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (0.2 g, 0.67 mmol) in DME (10 mL) were added (2-chlorophenyl)boronic acid, (0.137 g, 0.88 mmol), Pd tetrakis (20 mg, 10% mol/mol) and a 2M solution of sodium carbonate (1.34 mL, 4 eq). The reaction was heated at 85° C. for 48 hours. After evaporation of DME, water was added and the reaction was extracted with ethyl acetate (2×40 mL). The aqueous phase was adjusted to PH=7 by addition of a 1N HCl solution and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and evaporated in vacuo to give the title compound as a solid (117 mg, 40%). HRMS calculated for C17H14ClN3O2(M+H)+328.0853. found: 328.0865, Rt: 2.04 min.

Workup

  1. customAfter evaporation of DME, water
  2. additionwas added
  3. extractionthe reaction was extracted with ethyl acetate (2×40 mL)
  4. additionby addition of a 1N HCl solution
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic phases were dried over sodium sulphate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-ffac4b9241254689b09d4e71833884cf
Source dataset
uspto-grants-2015_06
Patent number
US09051281B2

Reaction notes

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