1,2-Dimethoxyethane → HCID 68292970, compound

HRID 2205400Notes

Reaction equation

HRID 2205400 reaction equation
Br[C:2]1[C:3]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:4][C:5](=[O:14])[N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.COCCOC.[CH3:28][N:29]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[N:30]1.C([O-])(O)=O.[Na+]>O.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>[CH3:28][N:29]1[CH:33]=[C:32]([C:2]2[C:3]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:4][C:5](=[O:14])[N:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:7]=2)[CH:31]=[N:30]1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 516892Sodium BicarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 68292775HCID 68292775, compound

Product 1

HCID 68292970HCID 68292970, compoundYield 29.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred mixture of 6-bromo-5-phenoxy-2-phenylpyridazin-3(2H)-one (see Example 2) (207 mg, 0.60 mmol), Pd(PPh3)4 (35 mg, 0.03 mmol) and degassed DME (9 mL), 1-methylpyrazole-4-boronic acid pinacol ester (150 mg, 0.72 mmol), and subsequently, a solution of NaHCO3 (102 mg, 1.2 mmol) in H2O (2.1 mL) were added. The reaction mixture was heated with vigorous stirring under Ar atmosphere at 80° C. for 12 h. The mixture was then evaporated under reduced pressure and the residue was purified by column chromatography on silica gel (n-hexane:EtOAc=1:1) to yield the desired compound as a white crystalline solid (61 mg, 29%). Mp 195-197° C., 1H NMR (400 MHz, CDCl3) δ 3.97 (s, 3H, CH3), 6.10 (s, 1H, H-4), 7.20 (d, 2H, J=7.6 Hz, C6H5), 7.33-7.55 (m, 6H, 2×C6H5), 7.64 (d, 2H, J=7.6 Hz, C6H5), 8.03 (s, 1H, NCH), 8.11 (s, 1H, NCH) ppm.

Workup

  1. temperatureThe reaction mixture was heated
  2. customThe mixture was then evaporated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (n-hexane:EtOAc=1:1)

Sources & evidence

ORD record
ord-210082b3ee5d40d19f2ec3d2d79d8a8d
Source dataset
uspto-grants-2016_06
Patent number
US09371290B2

Reaction notes

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