Lithium Chloride → HCID 178435843, compound

HRID 505856Notes

Reaction equation

HRID 505856 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:8]=[C:7]2[OH:18].[Cl-].[Li+].[CH2:21](C([SnH3])=C(CCCC)CCCC)[CH2:22]CC>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:12]1([C:9]2[CH:8]=[C:7]([OH:18])[C:6]3[C:11](=[C:2]([CH:21]=[CH2:22])[CH:3]=[CH:4][CH:5]=3)[N:10]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 21115800Tri(butyl)vinylstannaneHCID 178515550HCID 178515550, compound

Product 1

HCID 178435843HCID 178435843, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 500 mg (1.67 mmol) 8-bromo-2-phenyl-quinoline-4-ol (commercially available from Ubichem Research Ltd, Budapest, Hungary), 97 mg (0.09 mmol) Pd(PPh3)4, 71 mg (1.67 mmol) lithium chloride and 528 mg (1.67 mmol) tributylvinyl stannane in 20 ml dioxane was heated at 90° C. for 16 h. The resulting yellow suspension was filtered and the filtrate evaporated to dryness. The residue was suspended in ethyl acetate, filtered and the filtrate extracted with water. The organic layer was evaporated to dryness and the isolated crude product purified by silica gel chromatography (ethyl acetate) to yield 178 mg (43%) of the title compound as yellowish crystals. 1H-NMR (300 MHz, CDCl3): 5.59 (d, J=11.1 Hz, 1H); 5.75 (d, J=17.4 Hz, 1H); 6.42 (s, 1H); 7.04 (dd, J=17.4, 11.1 Hz, 1H); 7.23 (t, J=8.1 Hz, 1H); 7.40-7.60 (m, 6H); 8.21 (d, J=8.1 Hz, 1H); 8.70 (br, 1H).

Workup

  1. filtrationThe resulting yellow suspension was filtered
  2. customthe filtrate evaporated to dryness
  3. filtrationfiltered
  4. extractionthe filtrate extracted with water
  5. customThe organic layer was evaporated to dryness
  6. customthe isolated crude product
  7. custompurified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-afb114631abb4626ac7650d348cbc654
Source dataset
uspto-grants-2010_08
Patent number
US07781586B2

Reaction notes

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