Hydrochloric Acid → HCID 58873173, compound

HRID 1990094Notes

Reaction equation

HRID 1990094 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7]([O:9][C:10]([C:12]1[S:13][C:14]([CH2:32][CH3:33])=[C:15]([C:30]#[N:31])[C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])=[CH:19][CH:18]=1)=[O:11])[CH3:8].[CH2:34](I)[CH2:35][CH3:36].Cl>CN(C=O)C>[CH2:7]([O:9][C:10]([C:12]1[S:13][C:14]([CH2:32][CH3:33])=[C:15]([C:30]#[N:31])[C:16]=1[C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH2:34][CH2:35][CH3:36])=[CH:21][CH:22]=1)=[O:11])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 68522000HCID 68522000, compound

Product 1

HCID 58873173HCID 58873173, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add K2CO3 (220 mg, 1.6 mmol) to a solution of 4-cyano-5-ethyl-3-(2′-hydroxy-biphenyl-4-yl)-thiophene-2-carboxylic acid ethyl ester (200 mg, 0.53 mmol) in 2 mL of dry DMF at 0° C. and stir at this temperature for 1 hour. Treat with n-propyl iodide (0.2 mL, 2 mmol) and allow to warm to room temperature. After 3 hours pour into 25 mL cold 0.2N HCl. Extract with EtOAc (2×50 mL) and wash the combined EtOAc layers with water (2×20 mL) and brine (1×20 mL). Dry over Na2SO4, filter and evaporate to an oil. Chromatograph on silica gel (1/9-1/3 EtOAc/hexanes) to give the title compound as a tan solid, 158 mg (71%). HPLC=99%.

Workup

  1. extractionExtract with EtOAc (2×50 mL)
  2. washwash the combined EtOAc layers with water (2×20 mL) and brine (1×20 mL)
  3. dry with materialDry over Na2SO4
  4. filtrationfilter
  5. customevaporate to an oil

Sources & evidence

ORD record
ord-bab8e1141c2343b89cca1a595d13ea37
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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