Dichloromethane → HCID 66696623, compound

HRID 1672532Notes

Reaction equation

HRID 1672532 reaction equation
Br[C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=1[F:17].[CH2:18](Cl)Cl.C[Zn]C>O1CCOCC1.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]>[F:17][C:8]1[CH:9]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:11]=[CH:12][C:7]=1[C:6]1[O:5][CH:4]=[N:3][C:2]=1[CH3:18]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 66696590HCID 66696590, compoundHCID 178477796HCID 178477796, compound

Product 1

HCID 66696623HCID 66696623, compoundYield 2,596.4%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of Example 5B (4.58 g, 14.8 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II), 1:1 complex with CH2Cl2 (0.362 g, 0.443 mmol) in dioxane (49 mL) was treated carefully with dimethyl zinc (2M in toluene, 14.8 mL, 29.6 mmol). The reaction was heated to reflux for 2 hours, then cooled to room temperature and carefully quenched with a few milliliters of methanol. The mixture was diluted with ether and washed twice with 1N HCl and once with brine. The organic phase was dried over Na2SO4 and evaporated, then chromatographed (5 to 15% ethyl acetate-hexane) to afford the title compound as an orange oil (2.82 g, 78% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.52 (s, 1H), 7.87 (m, 2H), 7.74 (m, 1H), 2.27 (s, 3H). MS (DCI+) m/z 246 (M+H)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. customcarefully quenched with a few milliliters of methanol
  4. additionThe mixture was diluted with ether
  5. washwashed twice with 1N HCl and once with brine
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customevaporated
  8. customchromatographed (5 to 15% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-e1f559b4e23644cd8203daca85a0eef2
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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