Water → 2'-Cyano-5-(4-cyanopyridin-3-yl)-4'-methylbiphenyl-3-carboxylic acid

HRID 2278725Notes

Reaction equation

HRID 2278725 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH:13]=[C:12]([C:25]([O:27]C)=[O:26])[CH:11]=1)#[N:2].Br[C:30]1[CH:37]=[N:36][CH:35]=[CH:34][C:31]=1[C:32]#[N:33].C(=O)([O-])[O-].[Cs+].[Cs+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:34]2[CH:35]=[N:36][CH:37]=[CH:30][C:31]=2[C:32]#[N:33])[CH:13]=[C:12]([C:25]([OH:27])=[O:26])[CH:11]=1)#[N:2]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 110740513-Bromo-4-cyanopyridineHCID 58449393Methyl 2'-cyano-4'-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-3-carboxylate

Product 1

HCID 584493912'-Cyano-5-(4-cyanopyridin-3-yl)-4'-methylbiphenyl-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Into a 5 mL microwave vial were charged methyl 2′-cyano-4′-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-3-carboxylate (150 mg, 0.36 mmol), 3-bromoisonicotinonitrile (131 mg, 0.72 mmol), cesium carbonate (583 mg, 1.79 mmol), tetra-n-butylammonium iodide (132 mg, 0.36 mmol), POPd (18 mg, 0.036 mmol), water (0.3 mL) and N,N-dimethylformamide (1 mL). The reaction mixture was subjected to microwave irradiation at 150° C. for 10 mins. The reaction mixture was purified by HPLC to afford the title compound.

Workup

  1. customirradiation at 150° C. for 10 mins
  2. customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record
ord-c40630e0da4c4c11a83f3df84415dfa1
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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