Hydrochloric Acid → HCID 11238213, compound

HRID 1296691Notes

Reaction equation

HRID 1296691 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10](=[O:36])[O:11][C:12]2[C:17]([C:18]=1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[CH:22][CH:21]=1)=[CH:16][CH:15]=[C:14]([OH:34])[C:13]=2I.C([Sn](CCCC)(CCCC)[C:42]([O:44]CC)=[CH2:43])CCC.Cl.C(Cl)Cl>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:42]([C:13]1[C:14]([OH:34])=[CH:15][CH:16]=[C:17]2[C:12]=1[O:11][C:10](=[O:36])[C:9]([C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])=[C:18]2[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:22][CH:21]=1)(=[O:44])[CH3:43]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 58913103HCID 58913103, compound

Product 1

HCID 11238213HCID 11238213, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-(2,4-dichlorophenyl)-7-hydroxy-8-iodo-4-(4-(2-pyrrolidin-1-yl-ethoxy)-benzyl)-chromen-2-one (187 mg, 0.294 mmol), tributyl(1-ethoxyvinyl)tin (119 μL, 0.353 mmol) and Pd(Ph3P)4 (34 mg, 0.0294 mmol) in anhydrous dioxane (6 mL) was stirred at reflux temperature for 2 h. After cooling to room temperature, aqueous 1M HCl was added, and the resulting mixture was stirred for 20 min. CH2Cl2 was added and the layers were separated. The aqueous layer was further extracted with CH2Cl2 (2×). The combined organic layers were dried (MgSO4) and concentrated in vacuo. The resultant residue was purified using flash chromatography (silica gel, 19:1→9:1 CH2Cl2:MeOH) to afford a light brown solid (48 mg, 84% pure by HPLC) that was recrystallized from AcOEt/hexane to provide the title compound as a yellow solid (22 mg, 14%).

Workup

  1. temperatureat reflux temperature for 2 h
  2. stirringthe resulting mixture was stirred for 20 min
  3. customthe layers were separated
  4. extractionThe aqueous layer was further extracted with CH2Cl2 (2×)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified
  8. customto afford a light brown solid (48 mg, 84% pure by HPLC) that
  9. customwas recrystallized from AcOEt/hexane

Sources & evidence

ORD record
ord-853b08d500b94065990732a8ae62c9dc
Source dataset
uspto-grants-2007_07
Patent number
US07247646B2

Reaction notes

Loading…