Potassium Carbonate → HCID 89554491, compound

HRID 709516Notes

Reaction equation

HRID 709516 reaction equation
Br[C:2]1[N:7]=[C:6](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].CC1(C)C(C)(C)OB([C:29]2[CH:47]=[CH:46][C:32]([O:33][C:34]3[CH:35]=[CH:36][C:37]([C:42]([F:45])([F:44])[F:43])=[C:38]([CH:41]=3)[C:39]#[N:40])=[CH:31][CH:30]=2)O1>CN(C=O)C.O>[C:39]([C:38]1[CH:41]=[C:34]([CH:35]=[CH:36][C:37]=1[C:42]([F:43])([F:44])[F:45])[O:33][C:32]1[CH:46]=[CH:47][C:29]([C:2]2[N:7]=[C:6](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:4][CH:3]=2)=[CH:30][CH:31]=1)#[N:40]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 18472489HCID 18472489, compoundHCID 68093254HCID 68093254, compound

Product 1

HCID 89554491HCID 89554491, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

(E)-Ethyl 3-(6-(4-(3-cyano-4-(trifluoromethyl)phenoxy)phenyl)pyridin-2-yl)acrylate (13) was prepared as follows: A mixture of compound 11 (0.6 g, 1.0 eq), K2CO3 (2 eq), 5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-2-(trifluoromethyl)benzonitrile (12) (1.05 eq) and Pd[(o-toly)3P]2Cl2 (0.2 eq) in 10 mL of DMF and water (0.1 mL) was flushed with argon and then shaken at 90° C. for 3 h. After cooling to room temperature, the reaction mixture was quenched with water (20 mL), and extracted with EtOAc. The organic layer was washed with brine, concentrated, and purified by column (EtOAc/hexanes 10/1) to afford compound 13 as a colorless oil (0.8 g): 1H-NMR (400 MHz, CDCl3) δ 8.07 (d, 2H, 8.9 Hz), 7.74-7.84 (m, 4H), 7.39-7.43 (m, 2H), 7.3-7.33 (m, 1H), 7.21 (d, 2H, 8.8 Hz), 7.12 (d, 1H, 15.8 Hz), 4.32 (q, 2H, 7.2 Hz), 1.38 (t, 3H, 7.0 Hz).

Workup

  1. custom(E)-Ethyl 3-(6-(4-(3-cyano-4-(trifluoromethyl)phenoxy)phenyl)pyridin-2-yl)acrylate (13) was prepared
  2. customwas flushed with argon
  3. temperatureAfter cooling to room temperature
  4. customthe reaction mixture was quenched with water (20 mL)
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with brine
  7. concentrationconcentrated
  8. custompurified by column (EtOAc/hexanes 10/1)

Sources & evidence

ORD record
ord-856d5fa70b11449cb42f791a72c4e8de
Source dataset
uspto-grants-2015_11
Patent number
US09181185B2

Reaction notes

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