Hydrochloric Acid → HCID 69517336, compound

HRID 855069Notes

Reaction equation

HRID 855069 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH3:13])[CH:11]=1)[O:8][CH:7]([C:14]([F:17])([F:16])[F:15])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2.[CH3:23]B1OB(C)OB(C)O1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.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>[CH3:13][O:12][C:10]1[CH:11]=[C:2]([CH3:23])[CH:3]=[C:4]2[C:9]=1[O:8][CH:7]([C:14]([F:17])([F:16])[F:15])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 69518550HCID 69518550, compound

Product 1

HCID 69517336HCID 69517336, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl 6-bromo-8-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate (0.40 g, 1.05 mmole), trimethylboroxine (0.33 g, 2.63 mmole), Pd(PPh3)4 (0.13 g, 0.11 mmole) and K2CO3 (0.58 g, 4.20 mmole) in anhydrous DMF (5.0 mL) was heated to 90° C. under a dry N2 atmosphere for 18 hrs. The contents were poured into 2.4 N HCl (20 ml) and extracted with EtOAc (2×20 mL). The combined extracts were washed with brine (20 mL), dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil which was subject to flash chromatography (silica gel) and eluted with 10% EtOAc/ hexanes to give a light yellow oil (0.23 g, 70%): GCMS m/z 316.0 (M+). 1H NMR (CDCl3/400 MHz) 7.64 (s, 1H), 6.74 (s, 1H), 6.63 (s, 1H), 5.70 (q, 1H, J=7.0 Hz), 4.28 (m, 2H), 3.85 (s, 3H), 2.26 (s, 3H), 1.32 (m, 3H).

Workup

  1. extractionextracted with EtOAc (2×20 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 a yellow oil which
  7. washeluted with 10% EtOAc/ hexanes

Sources & evidence

ORD record
ord-15473b7665b149bba2bdb13f924e0043
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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