Sodium Carbonate → HCID 70341698, compound

HRID 2038387Notes

Reaction equation

HRID 2038387 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[S:12][C:11]([C:13]([O:15]CC)=[O:14])=[N:10][C:9]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1.[C:25]([C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[C:31]([F:33])[CH:32]=1)#[N:26].[Cl-].[NH4+]>COCCOC.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:24][C:20]1[CH:19]=[C:18]([C:9]2[N:10]=[C:11]([C:13]([OH:15])=[O:14])[S:12][C:8]=2[C:29]2[CH:30]=[C:31]([F:33])[CH:32]=[C:27]([C:25]#[N:26])[CH:28]=2)[CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 23435605(3-Cyano-5-fluorophenyl)boronic acidHCID 70801641Ethyl 5-bromo-4-(3-chlorophenyl)-1,3-thiazole-2-carboxylate

Product 1

HCID 70341698HCID 70341698, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

At room temperature, 7.2 ml of an aqueous 2M sodium carbonate solution and 167 mg (0.144 mmol) of tetrakis(triphenylphosphine)palladium are added to 1.00 g (2.89 mmol) of the compound from Example 5A and 714 mg (4.33 mmol) of the boronic acid from Example 22A in 40 ml of DME, and the mixture is subsequently stirred at 80° C. for 24 h. A saturated aqueous ammonium chloride solution is added, and the reaction mixture is subsequently extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient). 606 mg (53% of theory) of the title compound having a purity of 90% are obtained.

Workup

  1. extractionthe reaction mixture is subsequently extracted with dichloromethane
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)
  6. customare obtained

Sources & evidence

ORD record
ord-152ee68b846f409b85961a50caac29ed
Source dataset
uspto-grants-2013_11
Patent number
US08575357B2

Reaction notes

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