1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 58266748, compound

HRID 1506032Notes

Reaction equation

HRID 1506032 reaction equation
Br[C:2]1[CH:15]=[N:14][C:5]2[NH:6][C:7]3[CH:12]=[N:11][C:10](Br)=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[CH3:16][N:17]1[CH:21]=[C:20](B2OC(C)(C)C(C)(C)O2)[CH:19]=[N:18]1>C(#N)C.C(=O)([O-])[O-].[Na+].[Na+].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>[CH3:16][N:17]1[CH:21]=[C:20]([C:2]2[CH:15]=[N:14][C:5]3[NH:6][C:7]4[CH:12]=[N:11][C:10]([C:20]5[CH:19]=[N:18][N:17]([CH3:16])[CH:21]=5)=[CH:9][C:8]=4[C:4]=3[CH:3]=2)[CH:19]=[N:18]1

Participants

6

Reactant 2

HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 58266686HCID 58266686, compound

Product 1

HCID 58266748HCID 58266748, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
140 °C

Procedure

A suspension of 3,6-dibromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole (9.3 mg, 28 μmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (17.8 mg, 85.3 μmol) and bis(triphenylphosphine)palladium(II) dichloride (1.0 mg, 14 μmol) in acetonitrile (0.18 mL) and 2N aqueous sodium carbonate solution was heated under microwave irradiation at 140° C. for 20 minutes. The reaction mixture was allowed to cool to ambient temperature and the resultant precipitate collected by filtration, and the solid washed sequentially with water, DCM, and 20% MeOH in DCM. The filtrate was combined, the layers separated, and the aqueous phase extracted into 20% MeOH inDCM. The combined organic phase was concentrated in vacuo and the resultant residue purified by flash chromatography (silica, 0-20% MeOH in DCM) to afford the title compound. 1H NMR (DMSO-D6, 400 MHz): 12.01 (s, 1H), 8.83 (m, 2H), 8.78 (m, 1H), 8.39 (s, 1H), 8.21 (d, J=9.4 Hz, 2H), 7.97 (d, J=7.0 Hz, 2H), 3.98-3.91 (s, 6H). LCMS (Method D): RT=7.53 min, M+H+=330.

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationthe resultant precipitate collected by filtration
  3. washthe solid washed sequentially with water, DCM, and 20% MeOH in DCM
  4. customthe layers separated
  5. extractionthe aqueous phase extracted into 20% MeOH inDCM
  6. concentrationThe combined organic phase was concentrated in vacuo
  7. customthe resultant residue purified by flash chromatography (silica, 0-20% MeOH in DCM)

Sources & evidence

ORD record
ord-c1fdb78308ea49f1836540fd5d63fdb2
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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