Potassium Phosphate, Tribasic → HCID 44553610, compound

HRID 1958471Notes

Reaction equation

HRID 1958471 reaction equation
Br[C:2]1[C:3]2[N:4]([CH:17]=[N:18][N:19]=2)[CH:5]=[C:6]([C:8]2[S:12][C:11]([NH:13][CH:14]([CH3:16])[CH3:15])=[N:10][CH:9]=2)[CH:7]=1.[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CCO.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>[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:2]1[C:3]2[N:4]([CH:17]=[N:18][N:19]=2)[CH:5]=[C:6]([C:8]2[S:12][C:11]([NH:13][CH:14]([CH3:16])[CH3:15])=[N:10][CH:9]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343542-Fluorophenylboronic acidHCID 58207992HCID 58207992, compound

Product 1

HCID 44553610HCID 44553610, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(8-bromo-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-N-isopropylthiazol-2-amine (19.6 mg, 0.0579 mmol) and 2-fluorophenylboronic acid (12.7 mg, 0.081 mmol) in toluene (0.58 mL) was degassed via nitrogen bubble, then was added Pd(PPh3)4 (3.3 mg, 0.003 mmol), aqueous K3PO4 (2 M, 58 μL, 0.116 mmol) and ethanol (84 μL). The reaction mixture was heated to 100° C. overnight, cooled to rt, diluted with EtOH (1 mL), filtered and concentrated. The residues were purified directly by reverse phase preparative HPLC and the product containing fractions were concentrated and neutralized with aqueous NaHCO3 to precipitate the product. The solids were filtered, washed and dried to give (9.7 mg, 47% yield). LCMS 354.23, Tr 3.50 min (Conditions A).

Workup

  1. customwas degassed via nitrogen
  2. custombubble
  3. temperaturecooled to rt
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residues were purified directly by reverse phase preparative HPLC
  7. additionthe product containing fractions
  8. concentrationwere concentrated
  9. customto precipitate the product
  10. filtrationThe solids were filtered
  11. washwashed
  12. customdried
  13. customto give (9.7 mg, 47% yield)
  14. customLCMS 354.23, Tr 3.50 min

Sources & evidence

ORD record
ord-b04c37d208e34016b67a8e0e2e8c6277
Source dataset
uspto-grants-2013_04
Patent number
US08410128B2

Reaction notes

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