Water → HCID 53836832, compound

HRID 1966695Notes

Reaction equation

HRID 1966695 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].CC1(C)C(C)(C)OB([C:18]2[CH:19]=[N:20][NH:21][CH:22]=2)O1.C([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C.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.CCOC(C)=O>[NH:20]1[CH:19]=[C:18]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[CH:22]=[N:21]1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 811292-BromobenzaldehydeHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 53836832HCID 53836832, compoundYield 39.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-bromobenzaldehyde (300 mg, 1.62 mmol) in DMF (10 mL) are added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (470 mg, 2.43 mmol), Pd(PPh3)4 (190 mg, 0.16 mmol) and 2M Na2CO3 (0.50 mL) at room temperature. The solution is heated to 100° C. for 1 hour in a microwave reactor, cooled and poured into water and EtOAc. Layers are separated and the aqueous phase extracted with EtOAc (1×10 mL). The combined organics are dried (MgSO4), filtered and are concentrated to give the crude product which is purified via flash chromatography (12 g silica gel, 0-10% MeOH/CH2Cl2). The product-containing fractions are combined and concentrated to give 2-(1H-pyrazol-4-yl)-benzaldehyde (110 mg, 39%) which is used without further purification.

Workup

  1. temperaturecooled
  2. customLayers are separated
  3. extractionthe aqueous phase extracted with EtOAc (1×10 mL)
  4. dry with materialThe combined organics are dried (MgSO4)
  5. filtrationfiltered
  6. concentrationare concentrated
  7. customto give the crude product which
  8. customis purified via flash chromatography (12 g silica gel, 0-10% MeOH/CH2Cl2)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b233909d6314455eb1e1036b78c60429
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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