Dichloromethane → HCID 69517917, compound

HRID 855130Notes

Reaction equation

HRID 855130 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[C:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:6]([C:14]([F:17])([F:16])[F:15])[O:7]2.[CH3:23]B1OB(C)OB(C)O1.C(Cl)Cl.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CCOC(C)=O.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].O>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:2]([CH3:23])=[C:3]2[C:8]=1[O:7][CH:6]([C:14]([F:17])([F:16])[F:15])[C:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:4]2

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 574072TrimethylboroxineHCID 69516629HCID 69516629, compound

Product 1

HCID 69517917HCID 69517917, compoundYield 74%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

The ethyl 5-bromo-8-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate from Example 24 a, Step 1 (2.3 g, 6.037 mmole), trimethylboroxine (0.84 mL, 6.04 mmole), PdCl2(dppf)2.CH2Cl2 (0.487 g, 0.604 mmole), and Cs2CO3 (5.9 g, 18.11 mmole) were mixed in dioxane with 10% water (15 mL). The mixture was heated to 110° C. for 6 hrs and r.t overnight. The mixture was diluted with EtOAc, the organic layer was washed with water and dried over MgSO4. The filtrate was concentrated and purified by Biotage chromatography with 5% EtOAc in hexane to give 1.41 g a yellow solid (74%): LCMS m/z 317.15 (M+H) at 6.225 min.

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried over MgSO4
  3. concentrationThe filtrate was concentrated
  4. custompurified by Biotage chromatography with 5% EtOAc in hexane

Sources & evidence

ORD record
ord-8702446340004289b55b7bf7112c119e
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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