Potassium Phosphate, Tribasic → HCID 24985363, compound

HRID 1014695Notes

Reaction equation

HRID 1014695 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[N:15]=[C:14]([C:16]2[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=2)[CH:13]=[CH:12][C:11]=1[N+:23]([O-])=O.ClC1N=C(NC2C=CC=C[C:35]=2[O:40]C)C([N+]([O-])=O)=CC=1.OC1C=C(B(O)O)C=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:22][C:18]1[CH:17]=[C:16]([C:14]2[N:15]=[C:10]3[N:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[O:2][CH3:1])[C:35](=[O:40])[NH:23][C:11]3=[CH:12][CH:13]=2)[CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 2842435HCID 2842435, compoundHCID 66699831HCID 66699831, compound

Product 1

HCID 24985363HCID 24985363, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
98 °C

Procedure

3-(6-(2-Methoxyphenylamino)-5-nitropyridin-2-yl)phenol. 6-Chloro-N-(2-methoxy-phenyl)-3-nitropyridin-2-amine (2.03 g, 7.27 mmol), 3-hydroxyphenylboronic acid (1.50 g, 10.90 mmol), palladium (II) acetate (0.489 g, 0.727 mmol), 1,1′-(bis(di-tertbutyl)phosphine)ferrocene (0.344 g, 0.727 mmol) and potassium phosphate (4.62 g, 21.81 mmol) were combined in dioxane and heated to 98° C. under nitrogen conditions for 16 h. Upon consumption of starting material (monitored by TLC), the reaction mixture was filtered through celite. The filtrate was condensed under reduced pressure to afford the crude product. The crude material was purified using Biotage silica gel chromatography (10-40% ethyl acetate in hexanes) to afford the title compound (1.48 g, 59%). MS (ESI) m/z 338.4 [M+1]+.

Workup

  1. customUpon consumption of starting material (monitored by TLC)
  2. filtrationthe reaction mixture was filtered through celite
  3. customcondensed under reduced pressure
  4. customto afford the crude product
  5. customThe crude material was purified

Sources & evidence

ORD record
ord-b06e59a20a50437e9a90d80766fd83a5
Source dataset
uspto-grants-2011_07
Patent number
US07981893B2

Reaction notes

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