Water → 2-Cyano-2''-hydroxymethyl-4-methyl-[1,1';3',1'']terphenyl-5'-carboxylic acid ethyl ester

HRID 2278726Notes

Reaction equation

HRID 2278726 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=2[C:15]#[N:16])[CH:7]=1.[OH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O.[C:32](=O)([O-])[O-].[Cs+].[Cs+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH2:20]([O:19][C:17]([C:4]1[CH:3]=[C:2]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH2:22][OH:21])[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=2[C:15]#[N:16])[CH:5]=1)=[O:18])[CH3:32]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 43742622-(Hydroxymethyl)phenylboronic AcidHCID 58449349Methyl 5-bromo-2'-cyano-4'-methylbiphenyl-3-carboxylate

Product 1

HCID 1176665832-Cyano-2''-hydroxymethyl-4-methyl-[1,1';3',1'']terphenyl-5'-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Into a 5 mL microwave vial were charged methyl 5-bromo-2′-cyano-4′-methylbiphenyl-3-carboxylate (95 mg, 0.29 mmol), 2-(hydroxymethyl)phenylboronic acid (87 mg, 0.57 mmol), cesium carbonate (466 mg, 1.43 mmol), tetra-n-butylammonium iodide (106 mg, 0.29 mmol), POPd (14 mg, 0.029 mmol), water (0.2 mL) and N,N-dimethylformamide (1 mL). The reaction mixture was subjected to microwave irradiation for 10 mins at 150° C. After cooling, the reaction mixture was extracted with ethylacetate. The organic layer was washed with brine, dried, and concentrated under reduced pressure to give the residue which was purified by HPLC to yield the title compound.

Workup

  1. customirradiation for 10 mins at 150° C
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with ethylacetate
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto give the residue which
  8. customwas purified by HPLC

Sources & evidence

ORD record
ord-bd2fb6ee09e64b0cb4204b7179b23921
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

Loading…