Sodium Carbonate → 2-Benzhydryl-5-(3,5-bis(4-methylnaphthalen-1-yl)phenyl)-2H-tetrazole

HRID 1472785Notes

Reaction equation

HRID 1472785 reaction equation
[CH:1]([N:14]1[N:18]=[N:17][C:16]([C:19]2[CH:24]=[C:23](Br)[CH:22]=[C:21](Br)[CH:20]=2)=[N:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31](B(O)O)=[CH:30][CH:29]=1.O1[CH2:46][CH2:45]OCC1.C(=O)([O-])[O-].[Na+].[Na+]>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.O>[CH:1]([N:14]1[N:18]=[N:17][C:16]([C:19]2[CH:24]=[C:23]([C:31]3[C:32]4[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:28]([CH3:27])=[CH:29][CH:30]=3)[CH:22]=[C:21]([C:1]3[C:2]4[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:45]([CH3:46])=[CH:9][CH:8]=3)[CH:20]=2)=[N:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27735114-Methyl-1-naphthaleneboronic acidHCID 68293616HCID 68293616, compound

Product 1

HCID 682936402-Benzhydryl-5-(3,5-bis(4-methylnaphthalen-1-yl)phenyl)-2H-tetrazoleYield 90%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A round-bottomed flask was charged with 2-benzhydryl-5-(3,5-dibromophenyl)-2H-tetrazole (282 mg, 0.60 mmol), 4-methylnaphthalen-1-ylboronic acid (251 mg, 1.32 mmol) and Pd(PPh3)4 (35 mg, 0.03 mmol). After degassed, dioxane (5 mL) and aqueous sodium carbonate (3 mL, 2M, 6.0 mmol) was added. The reaction mixture was heated to 90° C. until the reaction was complete. 30 mL of water was added, and the reaction mixture was extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulphate and then concentrated. The residue was purified by flash chromatography (hexane:CH2Cl2=2:1) to afford 0.32 g (90%) of product as a white solid.

Workup

  1. customAfter degassed
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (hexane:CH2Cl2=2:1)

Sources & evidence

ORD record
ord-331adcb0a95348c59d75da1e9db7cedd
Source dataset
uspto-grants-2015_04
Patent number
US09012655B2

Reaction notes

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