Dichloromethane → HCID 59242664, compound

HRID 1630465Notes

Reaction equation

HRID 1630465 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[N:16][C:17]([C:21]([F:24])([F:23])[F:22])=[C:18](I)[CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25]1([CH3:34])[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O.ClCCl.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[N:16][C:17]([C:21]([F:24])([F:23])[F:22])=[C:18]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[CH3:34])[CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 27332672-Methylphenyl boronic acidHCID 58257834HCID 58257834, compound

Product 1

HCID 59242664HCID 59242664, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-(5-iodo-6-trifluoromethyl-pyridazin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester (D10) (0.20 g, 0.436 mmol), o-tolylboronic acid (0.071 g, 0.523 mmol), 1,1′-bis(diphenylphosphino)ferrocenepalladium(II).dichloride, dichloromethane (0.022 g, 0.026 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.015 g, 0.026 mmol) and potassium phosphate (0.138 g, 0.654 mmol) in dioxane (8.5 ml) was stirred at 80° C. for 16 h. and then at 110° C. for 2 days. The mixture was then filtered through a pad of diatomaceous earth and the solvent was evaporated in vacuo. The residue was purified by column chromatography (silica gel; dichloromethane/methanol 70/30) to yield D11 (0.089 g, 48%) as a yellow solid. C21H25F3N4O2 requires 422; Found 423 (MH+).

Workup

  1. filtrationThe mixture was then filtered through a pad of diatomaceous earth
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was purified by column chromatography (silica gel; dichloromethane/methanol 70/30)

Sources & evidence

ORD record
ord-d87a6dd0a0a04bad8089bd08c8114543
Source dataset
uspto-grants-2014_07
Patent number
US08791120B2

Reaction notes

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