Potassium Phosphate, Tribasic → 2-[4'-Chloro-4-(pyrrolidine-1-carbonyl)-biphen-2-yl]-quinoline-6-carboxylic acid methyl ester

HRID 1788415Notes

Reaction equation

HRID 1788415 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:15]1[CH:20]=[C:19]([C:21]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:22])[CH:18]=[CH:17][C:16]=1OS(C(F)(F)F)(=O)=O)[CH:9]=[CH:8]2)=[O:4].[Cl:36][C:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[Li+].[Cl-]>O1CCOCC1.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>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:15]1[C:16]([C:40]3[CH:41]=[CH:42][C:37]([Cl:36])=[CH:38][CH:39]=3)=[CH:17][CH:18]=[C:19]([C:21]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:22])[CH:20]=1)[CH:9]=[CH:8]2)=[O:4]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 742994-Chlorophenylboronic acid2×HCID 433294Lithium ChlorideHCID 576029242-[5-(Pyrrolidine-1-carbonyl)-2-trifluoromethanesulfonyloxy-phenyl]-quinoline-6-carboxylic Acid Methyl Ester

Product 1

HCID 576029372-[4'-Chloro-4-(pyrrolidine-1-carbonyl)-biphen-2-yl]-quinoline-6-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Compound 21 (320 mg, 0.63 mmol), 4-chloro-phenylboronic acid (Compound 22, 148 mg, 0.94 mmol), 500 mg (2.35 mmol) of K3PO4, 27 mg (0.63 mmol) of LiCl and 36.5 mg (0.031 mmol) of Pd(PPh3)4 were dissolved in 30 mL dioxane (degassed). The mixture was refluxed under argon overnight. The black solution was filtered through a Celite pad, and evaporated to dryness to give Compound 23 as yellow oil which was used without further purification. MS: 471.16 (M+H+).

Workup

  1. temperatureThe mixture was refluxed under argon overnight
  2. filtrationThe black solution was filtered through a Celite pad
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-3bd090c8f47e4c028b7d041b07d55119
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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