Potassium Phosphate, Tribasic → HCID 70977671, compound

HRID 2281070Notes

Reaction equation

HRID 2281070 reaction equation
FC(F)(F)S(O[C:7]1[CH:19]=[CH:18][C:10]2[N:11]([CH2:14][CH:15]3[CH2:17][CH2:16]3)[N:12]=[N:13][C:9]=2[C:8]=1[Cl:20])(=O)=O.[OH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(=O)(O)[O-].[Na+]>O1CCOCC1.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Cl:20][C:8]1[C:9]2[N:13]=[N:12][N:11]([CH2:14][CH:15]3[CH2:17][CH2:16]3)[C:10]=2[CH:18]=[CH:19][C:7]=1[C:28]1[CH:29]=[CH:30][C:25]([CH2:24][OH:23])=[CH:26][CH:27]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 516892Sodium BicarbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 86711985HCID 86711985, compound

Product 1

HCID 70977671HCID 70977671, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl trifluoromethanesulfonate (1.1 g, 3.1 mmol) was dissolved in a mixture of 1,4-dioxane and water (15 mL:3.0 mL) and treated with [4-(hydroxymethyl)phenyl]boronic acid (0.70 g, 4.6 mmol), potassium phosphate (2.0 g, 9.2 mmol) and palladium(0) tetrakis(triphenylphosphine) (0.18 g, 0.15 mmol). The mixture was placed into a preheated oil bath at 90° C. for 1 hour. The mixture was cooled to ambient temperature, poured into sodium bicarbonate (150 mL, aqueous saturated) and extracted with ethyl acetate (2×250 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (100:0 to 0:100; hexane:ethyl acetate) to afford the titled compound.

Workup

  1. extractionextracted with ethyl acetate (2×250 mL)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (100:0 to 0:100; hexane:ethyl acetate)

Sources & evidence

ORD record
ord-30252485510b40fcb01047d331da7d99
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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