Potassium Carbonate → HCID 178477701, compound

HRID 1888253Notes

Reaction equation

HRID 1888253 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]#[N:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:13]1[CH2:18][CH2:17][N:16]([S:19]([CH2:22][CH3:23])(=[O:21])=[O:20])[CH2:15][CH2:14]1.[F:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[C:29]([F:31])[CH:30]=1.C(=O)([O-])[O-:36].[K+].[K+]>O1CCOCC1.O>[F:24][C:25]1[CH:26]=[C:27]([C:2]2[CH:3]=[C:4]3[C:8](=[C:9]([C:11]([NH2:12])=[O:36])[CH:10]=2)[NH:7][N:6]=[C:5]3[CH:13]2[CH2:14][CH2:15][N:16]([S:19]([CH2:22][CH3:23])(=[O:20])=[O:21])[CH2:17][CH2:18]2)[CH:28]=[C:29]([F:31])[CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 178477688HCID 178477688, compound2×

Product 1

HCID 178477701HCID 178477701, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Following the general procedure of Example 66, a mixture of 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indazole-7-carbonitrile (Intermediate 10) (61.3 mg, 0.125 mmols), 3,5-difluorophenyl boronic acid (59 mg, 0.375 mmols), potassium carbonate (104 mg, 0.75 mmol), and chloro(di-2-norbonylphosphine)-(2-dimethylaminomethyl-forrocen-1-yl)palladium (15 mg, 0.025 mmol) in dioxane/water (3/1, 4 mL) was reacted. The reaction mixture was concentrated, redissolved in methylene chloride and filtered. The filtrate was concentrated and the residue was purified by using a Gilson semi-preparative HPLC system, eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) pumped at 25 mL/min to give the title compound (15 mg, 33%)

Workup

  1. customwas reacted
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionredissolved in methylene chloride
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified
  7. washeluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-935af53868d34e5cafc43464656e5068
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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