Cesium carbonate → HCID 46869636, compound

HRID 1912478Notes

Reaction equation

HRID 1912478 reaction equation
Cl[C:2]1[C:7]2[N:8]=[C:9]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[N:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=3)[C:6]=2[N:5]=[C:4]([C:25]([OH:27])=[O:26])[CH:3]=1.[C:28]1(B(O)O)[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.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>[OH:18][C:14]1[CH:13]=[C:12]([C:11]2[C:6]3[N:5]=[C:4]([C:25]([OH:27])=[O:26])[CH:3]=[C:2]([C:36]4[C:37]5[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH:33]=[CH:34][CH:35]=4)[C:7]=3[N:8]=[C:9]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[N:10]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2545321-Naphthaleneboronic acidHCID 46869088HCID 46869088, compound

Product 1

HCID 46869636HCID 46869636, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 9 (145 mg; 0.37 mmol), 1-naphthylboronic acid (142 mg; 0.82 mmol), cesium carbonate (489 mg; 1.50 mmol) and Pd(PPh3)4 (87 mg; 0.07 mmol) in DMF (4 mL) was stirred at 150° C. for one hour (microwave heating) then concentrated in vacuo. The residue was partitioned between EA and aq. citric acid and the two phases separated. The aqueous layer was dried over magnesium sulfate and concentrated in vacuo. Precipitation from EA/Et2O afforded the title compound as a yellow solid.

Workup

  1. temperature(microwave heating)
  2. concentrationthen concentrated in vacuo
  3. customThe residue was partitioned between EA and aq. citric acid
  4. customthe two phases separated
  5. dry with materialThe aqueous layer was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customPrecipitation from EA/Et2O

Sources & evidence

ORD record
ord-27bce762a65c46b590dab8b8a3b0da17
Source dataset
uspto-grants-2013_12
Patent number
US08609666B2

Reaction notes

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