Dichloromethane → HCID 59811950, compound

HRID 2114041Notes

Reaction equation

HRID 2114041 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([N:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=4)[CH:18]=[C:13]3[C:12](I)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClCCl.C(N(CC)CC)C.[CH3:39][C:40]1([CH3:47])[C:44]([CH3:46])([CH3:45])[O:43][BH:42][O:41]1>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]>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([N:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=4)[CH:18]=[C:13]3[C:12]([B:42]3[O:43][C:44]([CH3:46])([CH3:45])[C:40]([CH3:47])([CH3:39])[O:41]3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 59811927HCID 59811927, compound

Product 1

HCID 59811950HCID 59811950, compoundYield 115.6%

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 3 (0.50 g, 0.99 mmol), [1,1′-bis(diphenylphosphino) ferrocene dichloropalladium(II).dichloromethane complex [PdCl2(dppf)2.CH2Cl2] (24.3 mg, 0.0298 mmol), triethylamine (415 μL, 2.98 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (221 μL, 1.52 mmol) in dioxane (5.0 mL) was microwaved at 120° C. for 0.5 h. The reaction mixture was cooled, poured onto water (100 mL), extracted with ethyl acetate (4×30 mL), the combined organic extracts washed with brine (30 mL), dried (MgSO4) and concentrated. This gave the product 16 as a brown foam (576 mg, 113%) which was used in the next step without further purification; 1H NMR (400 MHz, CDCl3) δ 1.38 (s, 12H), 3.02 (s, 6H), 6.86 (d, J=8.8 Hz, 2H), 7.65-7.45 (m, 5H), 8.16 (s, 1H), 8.26 (d, J=7.4 Hz, 2H), 8.30 (d, J=2.2 Hz, 1H), 8.63 (d, J=2.2 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionpoured onto water (100 mL)
  3. extractionextracted with ethyl acetate (4×30 mL)
  4. washthe combined organic extracts washed with brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0d04174b23454275a39535f812e1524d
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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