Triethylamine → 1350378-37-8

HRID 2362706Notes

Reaction equation

HRID 2362706 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2I.C(N(CC)CC)C.[CH3:20][C:21]1([CH3:28])[C:25]([CH3:27])([CH3:26])[O:24][BH:23][O:22]1>O1CCOCC1.C(OCC)(=O)C.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].ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[B:23]1[O:24][C:25]([CH3:27])([CH3:26])[C:21]([CH3:28])([CH3:20])[O:22]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 670034711350378-38-9

Product 1

HCID 670035221350378-37-8

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 5-fluoro-3-iodo-1-methyl-1H-indole (11.5 g, 41.8 mmol) in dioxane (200 mL) was treated with triethyl amine (27 mL, 194 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane (1.707 g, 2.090 mmol). 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane (39.4 mL, 272 mmol) was added carefully to the reaction (gas evolution was observed). The mixture was heated to 100° C. for 30 minutes, cooled, and diluted with about 250 mL ethyl acetate. The precipitate was filtered and washed with ethyl acetate (100 mL). The filtrate was concentrated under reduced pressure. The residue was purifed on silica gel, eluting with 8:2 heptane:ethyl acetate, to give the title compound. MS ESI(+) m/z 276.0 (M+H)+.

Workup

  1. temperaturecooled
  2. filtrationThe precipitate was filtered
  3. washwashed with ethyl acetate (100 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. washeluting with 8:2 heptane

Sources & evidence

ORD record
ord-b21849c451914a7aac59fac3bad305a2
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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