Triethylamine → HCID 67279752, compound

HRID 1694690Notes

Reaction equation

HRID 1694690 reaction equation
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][C:7](Br)=[C:6]([CH3:11])[CH:5]=1)[CH3:2].[CH3:12][C:13]1([CH3:20])[C:17]([CH3:19])([CH3:18])[O:16][BH:15][O:14]1.C(N(CC)CC)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][C:7]([B:15]2[O:16][C:17]([CH3:19])([CH3:18])[C:13]([CH3:20])([CH3:12])[O:14]2)=[C:6]([CH3:11])[CH:5]=1)[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 59350852HCID 59350852, compound

Product 1

HCID 67279752HCID 67279752, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of the product from step (i) (6.6 g), 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane (1.94 ml), triethylamine (2.4 ml), palladium acetate (0.06 g) and 2-(dicyclohexylphosphino) biphenyl (0.3 g) in dioxane (20 ml) was heated at 85° C. for 2 h. The mixture was quenched with aqueous ammonium chloride solution, extracted with diethylether, the organics dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 50% isohexane/DCM. Yield 0.7 g

Workup

  1. customThe mixture was quenched with aqueous ammonium chloride solution
  2. extractionextracted with diethylether
  3. customthe organics dried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by chromatography on silica eluting with 50% isohexane/DCM

Sources & evidence

ORD record
ord-1e82cc8060ed412482dc6da88f479bc0
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

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