Potassium Phosphate, Tribasic → 5-(2-chloro-4-(trifluoromethyl)phenyl)-N-(pyrimidin-4-yl)naphthalene-2-sulfonamide

HRID 1473311Notes

Reaction equation

HRID 1473311 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([NH:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][N:17]=1)(=[O:14])=[O:13])=[CH:7]2.[Cl:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:24]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(C1C(C(C)(C)C)=C([Pd]Cl)C=CC=1NC)(C)(C)C.CCOC(C)=O>[Cl:22][C:23]1[CH:28]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:26]=[CH:25][C:24]=1[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([NH:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][N:17]=1)(=[O:14])=[O:13])=[CH:7]2

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2783251[2-Chloro-4-(trifluoromethyl)phenyl]boronic acidHCID 866873675-bromo-N-(pyrimidin-4-yl)naphthalene-2-sulfonamide2×

Product 1

HCID 866873685-(2-chloro-4-(trifluoromethyl)phenyl)-N-(pyrimidin-4-yl)naphthalene-2-sulfonamideYield 75%

Reagents, catalysts & solvents 2

HCID 178482226HCID 178482226, compoundCatalystHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
90 °C

Procedure

A microwave vial was charged with 5-bromo-N-(pyrimidin-4-yl)naphthalene-2-sulfonamide (Intermediate W) (0.508 g, 1.395 mmol), (2-chloro-4-(trifluoromethyl)phenyl)boronic acid (0.469 g, 2.092 mmol), potassium phosphate (0.888 g, 4.18 mmol), and 1,1-bis[(di-t-butyl-p-methylaminophenyl]palladium(ii) chloride (0.099 g, 0.139 mmol). The vial was sealed with a septum cap and flushed with N2. Dioxane (3.49 mL) and water (1.162 mL) were added and the mixture was sparged for 5 min with N2. The mixture was heated in a microwave at 90° C. for 30 min. The resulting mixture was diluted with EtOAc (5 mL) and decanted from insoluble solids. The resulting solution was concentrated for purification by MPLC. The residue was taken up in minimal CH2Cl2 and absorbed onto a 5 g loading cartridge and passed through a silica gel column (12 g) using a 98:2 Heptane:EtOAc (with 5% EtOH additive) to 100% EtOAc (5% EtOH additive) gradient to afford 5-(2-chloro-4-(trifluoromethyl)phenyl)-N-(pyrimidin-4-yl)naphthalene-2-sulfonamide (0.485 g, 1.046 mmol) as a orange amorphous solid.

Workup

  1. customThe vial was sealed with a septum
  2. customcap
  3. customflushed with N2
  4. additionDioxane (3.49 mL) and water (1.162 mL) were added
  5. customthe mixture was sparged for 5 min with N2
  6. additionThe resulting mixture was diluted with EtOAc (5 mL)
  7. customdecanted from insoluble solids
  8. concentrationThe resulting solution was concentrated for purification by MPLC
  9. customabsorbed onto a 5 g loading cartridge

Sources & evidence

ORD record
ord-da7aad69807f466191e92d93a9268dd8
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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