Water → HCID 22031031, compound

HRID 1792591Notes

Reaction equation

HRID 1792591 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[N:15]=[C:14]([CH:16]4[CH2:18][CH2:17]4)[O:13][N:12]=3)=[CH:9][N:10]=2)[CH:7]=1.[F:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[C:28]1[C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][N:30]([C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[N:29]=1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CN(C)C=O.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.C(OCC)(=O)C>[CH:16]1([C:14]2[O:13][N:12]=[C:11]([C:8]3[N:6]4[CH:7]=[C:2]([C:32]5[C:28]([C:21]6[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:20]=6[F:19])=[N:29][N:30]([C:42]([C:55]6[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=6)([C:43]6[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=6)[C:49]6[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=6)[CH:31]=5)[CH:3]=[CH:4][C:5]4=[N:10][CH:9]=3)[N:15]=2)[CH2:18][CH2:17]1

Participants

8

Reactant 4

HCID 962WaterHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 22031890HCID 22031890, compoundHCID 22032326HCID 22032326, compound

Product 1

HCID 22031031HCID 22031031, compoundYield 73.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

82 mg 6-bromo-3-(5-cyclopropyl-[1,2,4]oxadiazol-3-yl)-imidazo[1,2-a]pyridine (compound in Production Example 255), 227 mg 3-(2-fluoro-4-methoxyphenyl)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-trityl-1H-pyrazole (compound in Production Example 185), 86 mg tripotassium phosphate hydrate and 31 mg tetrakis(triphenylphosphine)palladium were stirred at 80° C. for 14 hours in 3 mL N,N-dimethylformamide under nitrogen atmosphere. Water and ethyl acetate were added thereto, then the reaction solution was filtered through Celite, and the organic layer was washed with brine. The solution was dried over anhydrous sodium sulfate, the solvent was removed, and the resulting residue was purified by NH silica gel column chromatography (hexane/ethyl acetate) to give 130 mg of the title compound (colorless oil).

Workup

  1. filtrationthe reaction solution was filtered through Celite
  2. washthe organic layer was washed with brine
  3. dry with materialThe solution was dried over anhydrous sodium sulfate
  4. customthe solvent was removed
  5. customthe resulting residue was purified by NH silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a60b2d0c17744fa783349fd6aea95e60
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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