Potassium Carbonate → HCID 11752793, compound

HRID 1296690Notes

Reaction equation

HRID 1296690 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:37]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1>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>[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]=2[CH3:37]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 58913103HCID 58913103, compound

Product 1

HCID 11752793HCID 11752793, compound

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 (1.85 g, 2.91 mmol), K2CO3 (1.21 g, 8.75 mmol), trimethylboroxine (427 μL, 3.05 mmol) and Pd(Ph3P)4 (336 mg, 0.29 mmol) in anhydrous dioxane (22 mL) was stirred at reflux temperature for 2.5 h. After cooling the resultant green suspension to room temperature, the solvent was removed in vacuo. The resultant residue was dissolved in CH2Cl2, and the organic layer was washed with H2O and brine, dried (MgSO4) concentrated in vacuo. The resultant residue was purified using flash chromatography (125 g silica gel, 8:0.5:0.5→7:0.5:0.5 CH2Cl2:MeOH:AcOEt→9:1 CH2Cl2:MeOH) to afford a yellow solid that was further purified using reverse phase HPLC (followed by an extraction with CH2Cl2/NaHCO3). The title compound was isolated as a yellow solid (220.4 mg, 14%). 1H NMR (300 MHz, CDCl3) δ 7.48 (d, J=2.0 Hz, 1H), 7.24 (dd, J=2.0, 8.0 Hz, 1H), 7.18 (d, J=8.8 Hz, 1H), 7.12 (d, J=8.0 Hz, 1H), 6.90 (d, J=8.8 Hz, 2H), 6.84 (d, J=8.8 Hz, 1H), 6.72 (d, J=8.8 Hz, 2H), 4.23 (t, J=5.0 Hz, 2H), 4.00 (d, J=15.5 Hz, 1H), 3.74 (d, J=15.5 Hz, 1H), 3.24 (t, J=5.0 Hz, 2H), 3.15–3.04 (m, 4H), 2.20 (s, 3H), 2.05–1.93 (m, 4H); MS (ESI) m/z 523.8 (M)+; HPLC tR 4.74 min.

Workup

  1. temperatureat reflux temperature for 2.5 h
  2. customthe solvent was removed in vacuo
  3. dissolutionThe resultant residue was dissolved in CH2Cl2
  4. washthe organic layer was washed with H2O and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified
  8. customMeOH:AcOEt→9:1 CH2Cl2:MeOH) to afford a yellow solid
  9. customthat was further purified
  10. extractionfollowed by an extraction with CH2Cl2/NaHCO3)

Sources & evidence

ORD record
ord-8b4f9fa67c1a4f2290257a8e97b07866
Source dataset
uspto-grants-2007_07
Patent number
US07247646B2

Reaction notes

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