Ethanol → HCID 67126112, compound

HRID 514038Notes

Reaction equation

HRID 514038 reaction equation
[CH2:1]([O:3][C:4](=[O:37])[CH:5]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[C:6]1[C:15]([CH3:16])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[O:17][CH3:18])[C:7]=1OS(C(F)(F)F)(=O)=O)[CH3:2].[Cl:38][C:39]1[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1.CCO.C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[Pd].C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:37])[CH:5]([C:6]1[C:15]([CH3:16])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[O:17][CH3:18])[C:7]=1[C:42]1[CH:43]=[CH:44][C:39]([Cl:38])=[CH:40][CH:41]=1)[O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[CH3:2]

Participants

8

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 86691541HCID 86691541, compound

Product 1

HCID 67126112HCID 67126112, compoundYield 50.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of (4-methoxy-benzyloxy)-(5-methoxy-3-methyl-1-trifluoromethanesulfonyloxy-naphthalen-2-yl)-acetic acid ethyl ester (128 mg, 0.236 mmol), 4-chlorophenylboronic acid (74 mg, 2 equiv), EtOH (0.5 mL), K2CO3 (2 M, 0.5 mL), and toluene (1.3 mL) were degassed with argon at room temperature in a Schlenk tube. Pd(dppf)Cl2 was then added (17 mg) and the tube sealed. The reaction was heated to 60° C. for 14 hours. Analysis of the reaction mixture by LCMS showed 40% conversion, with visual analysis showing significant amount of palladium black. The crude mixture was filtered via syringe through a microfilter into a new sealable tube charged with Pd(PPh3)4. The tube was sealed and heated to 100° C. for 16 hours. The reaction was cooled to room temperature, diluted with EtOAc and filtered through Celite. The filtrate was concentrated, and the crude residue purified by flash column chromatography to give the desired product (60 mg, 50% yield). LCMS-ESI+ (m/z): [M+Na]+ calcd for C30H29ClNaO5: 527.99. Found: 527.44.

Workup

  1. customthe tube sealed
  2. filtrationThe crude mixture was filtered via syringe through a microfilter into a new sealable tube
  3. additioncharged with Pd(PPh3)4
  4. customThe tube was sealed
  5. temperatureheated to 100° C. for 16 hours
  6. temperatureThe reaction was cooled to room temperature
  7. additiondiluted with EtOAc
  8. filtrationfiltered through Celite
  9. concentrationThe filtrate was concentrated
  10. customthe crude residue purified by flash column chromatography

Sources & evidence

ORD record
ord-7fc128cacef0495f9268dc58db6d5488
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

Loading…