Water → HCID 69517414, compound

HRID 855103Notes

Reaction equation

HRID 855103 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[NH:12][CH2:13][CH:14]([CH3:16])[CH3:15])[O:8][CH:7]([C:17]([F:20])([F:19])[F:18])[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5]2.[CH3:26]B1OB(C)OB(C)O1.C([O-])([O-])=O.[Cs+].[Cs+].O>COCCOCCOC>[CH2:13]([NH:12][C:11]1[CH:10]=[C:9]2[C:4]([CH:5]=[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:7]([C:17]([F:20])([F:19])[F:18])[O:8]2)=[CH:3][C:2]=1[CH3:26])[CH:14]([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 574072TrimethylboroxineHCID 69518625HCID 69518625, compound

Product 1

HCID 69517414HCID 69517414, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of ethyl 6-chloro-7-(isobutylamino)-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 608b, Step 1 (2.10 g, 5.57 mmole), trimethylboroxine (1.58 mL, 12.66 mmole), [(tBu3P)PdBr]2 (0.04 g), and Cs2CO3 (3.17 g, 9.74 mmole) in anhydrous diglyme (10.0 mL) was heated to 115° C. under a dry N2 atmosphere for 18 hrs. The contents were poured into water (40 ml) and extracted with EtOAc (2×40 mL). The combined extracts were washed with brine (20 mL), dried over MgSO4, filtered and concentrated in vacuo to give an orange oil which was subject to flash chromatography (silica gel) and eluted with 0-15% EtOAc/hexanes to give yellow oil (0.5 g, 25%). No further purification was performed. GCMS m/z 357.0 (M+). LCMS m/z 358.0 (M+H).

Workup

  1. extractionextracted with EtOAc (2×40 mL)
  2. washThe combined extracts were washed with brine (20 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an orange oil which
  7. washeluted with 0-15% EtOAc/hexanes

Sources & evidence

ORD record
ord-9858b0ef57d449d0ac412bfd15979189
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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