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Dichloromethane → HCID 22032903, compound

HRID 1828219
Notes
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Reaction equation

HRID 1828219 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]([F:31])([F:30])[O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.ClCCl.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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]>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:24]3[CH:23]=[CH:22][C:21]([O:20][C:19]([F:18])([F:30])[F:31])=[CH:26][CH:25]=3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 2857561-Benzyl-5-Bromo-1H-IndoleHCID 27343864-(Trifluoromethoxy)phenylboronic acid

Product 1

HCID 22032903HCID 22032903, compoundYield 42.3%

Reagents, catalysts & solvents 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
77 °C

Procedure

A mixture of 1-benzyl-5-bromo-1H-indole (5.2 g, 18 mmol), 4-trifluoromethoxyphenylboronic acid (4.7 g, 23 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.88 g, 1.1 mmol), potassium carbonate (3.8 g, 27 mmol) in dioxane (135 mL) and water (13.5 mL) was heated at 77° C. for 5 hours. The reaction mixture was evaporated to dryness and partitioned in ethyl acetate and 2N hydrochloric acid. The organic phase was washed with water and brine, dried over anhydrous anhydrous magnesium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography (Biotage apparatus) using hexane as an eluant to yield the title compound as a light yellow wax/solid (2.8 g, 42%), mp 62–63° C. 1HNMR (300 MHz, DMSO-d6): δ7.85 (s, 1H), 7.75 (d, 2H, J=7.7 Hz), 7.5–7.6 (m, 2H), 7.4 (d, 3H, J=7.7 Hz), 7.2-7.35 (m, 5H), 6.6 (d, 1H, J=3.9 Hz), and 5.45 ppm (s, 2H).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. custompartitioned in ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography (Biotage apparatus)

Sources & evidence

ORD record
ord-db4aea6f30ae4c04b990af51ee7c3efc
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07056943B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes