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Triethylamine → 5-fluoro-1-methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

HRID 2362706
Notes
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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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 670034715-fluoro-3-iodo-1-methyl-1H-indole

Product 1

HCID 670035225-fluoro-1-methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalyst
HCID 8857
Ethyl Acetate
Solvent
HCID 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08691810B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes