Sodium Carbonate → HCID 136367320, compound

HRID 2234123Notes

Reaction equation

HRID 2234123 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[CH:15]=2)[CH:10]=[C:9]1[C:25]1[CH:30]=[C:29](Cl)[N:28]=[N:27][C:26]=1[O:32][CH3:33])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:34][C:35]1[CH:40]=[C:39](B2OC(C)(C)C(C)(C)O2)[CH:38]=[C:37]([CH3:50])[C:36]=1[OH:51].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.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>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[CH:15]=2)[CH:10]=[C:9]1[C:25]1[CH:30]=[C:29]([C:39]2[CH:38]=[C:37]([CH3:50])[C:36]([OH:51])=[C:35]([CH3:34])[CH:40]=2)[N:28]=[N:27][C:26]=1[O:32][CH3:33])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27346492,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 86612058HCID 86612058, compound

Product 1

HCID 136367320HCID 136367320, compoundYield 90.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

500 mg 2-(6-Chloro-3-methoxy-pyridazin-4-yl)-6-(4-methyl-piperazin-1-ylmethyl)-indole-1-carboxylic acid tert-butyl ester, 233 mg 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 180 mg sodium carbonate, and 98 mg tetrakis(triphenylphosphine)palladium(0) are dissolved in a mixture of 6.7 mL dimethoxyethane and 0.85 mL water. Argon is bubbled through the solution for 5 minutes. The mixture is heated to reflux for 5 hours. After diluting with EtOAc, the organic phase is washed with water and brine, dried with MgSO4 and concentrated in vacuo. 475 mg crude product are obtained.

Workup

  1. customArgon is bubbled through the solution for 5 minutes
  2. temperatureThe mixture is heated
  3. temperatureto reflux for 5 hours
  4. additionAfter diluting with EtOAc
  5. washthe organic phase is washed with water and brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b55c9b7124994465a5196bf52853e8cb
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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