Potassium Phosphate, Tribasic → HCID 9981742, compound

HRID 857684Notes

Reaction equation

HRID 857684 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][C:12]3[N:17]=[CH:16][N:15]=[C:14]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:19]=4OS(C(F)(F)F)(=O)=O)[CH:13]=3)[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[F: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+].[K+].[Br-]>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>[F:36][C:37]1[CH:42]=[CH:41][C:40]([C:19]2[CH:20]=[C:21]([C:24]([F:25])([F:27])[F:26])[CH:22]=[CH:23][C:18]=2[C:14]2[N:15]=[CH:16][N:17]=[C:12]([O:11][C:8]3[CH:9]=[C:10]4[C:5]([CH:4]=[CH:3][CH:2]=[N:1]4)=[CH:6][CH:7]=3)[CH:13]=2)=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 253877Potassium BromideHCID 2856454-Fluorophenylboronic acidHCID 58759740HCID 58759740, compound

Product 1

HCID 9981742HCID 9981742, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of trifluoromethanesulfonic acid 2-[6-(quinolin-7-yloxy)-pyrimidin-4-yl]-5-trifluoromethylphenyl ester, (Example 192(a)), (100 mg, 0.19 mmol), 4-fluorophenyl boronic acid (41 mg, 0.29 mmol, Aldrich), K3PO4 (82 mg, 0.39 mmol), KBr (35 mg, 0.29 mmol) and Pd(PPh3)4 (11 mg, 0.010 mmol, Strem) in dioxane (2.0 mL) was stirred and heated by microwave synthesizer at 140° C. for 10 min. The mixture was partitioned between CH2Cl2 and 1 N NaOH. The organic phase was separated, and the aqueous phase was extracted with CH2Cl2. The combined extracts were dried over Na2SO4, filtered and concentrated in vacuum. Purification by silica gel chromatography (gradient 0.5 to 3.0 % MeOH/CH2Cl2) afforded the title compound as a white amorphous solid. MS (ESI, pos. ion) m/z: 462 (M+1).

Workup

  1. customThe mixture was partitioned between CH2Cl2 and 1 N NaOH
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with CH2Cl2
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customPurification by silica gel chromatography (gradient 0.5 to 3.0 % MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-266d7d443c28468086c3931677fd47a8
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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