Sodium Carbonate → HCID 136339638, compound

HRID 1786675Notes

Reaction equation

HRID 1786675 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([O:8][CH3:9])=[C:4]([C:10](=[O:12])[CH3:11])[CH:3]=1.[CH3:13][C:14]1[CH:19]=[C:18](B2OC(C)(C)C(C)(C)O2)[CH:17]=[C:16]([CH3:29])[C:15]=1[OH:30].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:30][C:15]1[C:16]([CH3:29])=[CH:17][C:18]([C:2]2[N:7]=[N:6][C:5]([O:8][CH3:9])=[C:4]([C:10](=[O:12])[CH3:11])[CH:3]=2)=[CH:19][C:14]=1[CH3:13]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27346492,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 230924911-(6-Chloro-3-methoxy-4-pyridazinyl)ethanone

Product 1

HCID 136339638HCID 136339638, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

250 mg of 1-(6-Chloro-3-methoxy-pyridazin-4-yl)-ethanone and 232 mg of tetrakis(triphenylphosphine) palladium (0) are dissolved in 5 ml DME and the solution is stirred for 5 min at RT under argon. 400 mg of 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol and 1.4 ml of a 2M aqueous solution of sodium carbonate are added and the reaction solution is stirred at 95° C. for 4 h. The reaction solution is filtered through a silica gel cartridge, eluting with dichloromethane. The solvent is removed under reduced pressure. The product is purified by silica gel chromatography, eluting with a gradient of ethyl acetate in heptane. Yield 334 mg. LC-MS (ES+) 273 (M+H)+.

Workup

  1. stirringthe reaction solution is stirred at 95° C. for 4 h
  2. filtrationThe reaction solution is filtered through a silica gel cartridge
  3. washeluting with dichloromethane
  4. customThe solvent is removed under reduced pressure
  5. customThe product is purified by silica gel chromatography
  6. washeluting with a gradient of ethyl acetate in heptane

Sources & evidence

ORD record
ord-37ce4e5a8ef842b18b2e9b12bd3cff77
Source dataset
uspto-grants-2009_03
Patent number
US07507734B2

Reaction notes

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