Sodium Carbonate → HCID 22990571, compound

HRID 1169285Notes

Reaction equation

HRID 1169285 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[C:9]([Cl:15])[C:8]=1[Cl:16])(=O)=O.[C:19]1(B(O)O)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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>[Cl:15][C:9]1[C:8]([Cl:16])=[C:7]([C:27]2[C:28]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:24]=[CH:25][CH:26]=2)[CH:12]=[CH:11][C:10]=1[CH:13]=[O:14]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 110563872,3-dichloro-4-formylphenyl trifluoromethanesulfonate

Product 1

HCID 22990571HCID 22990571, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of Example 5A (0.20 g, 0.62 mmol), 1-naphthylboronic acid (0.13 g, 0.74 mmol), Pd(PPh3)4 (20 mg), and 2M Na2CO3 (0.62 mL) in toluene (2.0 mL) was heated to 100° C., stirred for 16 hours, and concentrated. The concentrate was purified by flash column chromatography on silica gel with hexanes to 5:1 hexanes/ethyl acetate to provide the desired product.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash column chromatography on silica gel with hexanes to 5:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-608c1e9209bf4ba0bd8b23dbe4eeafe1
Source dataset
uspto-grants-2003_09
Patent number
US06627767B2

Reaction notes

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