Water → HCID 71295584, compound

HRID 1776805Notes

Reaction equation

HRID 1776805 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([C:10]#[CH:11])[CH:3]=1.Br[C:13]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=1[NH:20]C(=O)C(F)(F)F.O>CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([C:10]2[NH:20][C:14]3[C:13]([CH:11]=2)=[C:18]([F:19])[CH:17]=[CH:16][CH:15]=3)[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 15691441HCID 15691441, compoundHCID 232607034-Chloro-2-ethynyl-1-methoxybenzene

Product 1

HCID 71295584HCID 71295584, compoundYield 25.9%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 2724141Tetrabutylammonium FluorideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-chloro-2-ethynyl-1-methoxybenzene (255 mg, 1.5 mmol), N-(2-bromo-3-fluorophenyl)-2,2,2-trifluoroacetamide (400 mg, 1.4 mmol), Pd(PPh3)2Cl2 (30 mg, 0.04 mmol) was stirred in TBAF.3H2O (1.43 g, 7 mmol) at 110° C. for 12 hours. The reaction mixture was cooled to 25° C. and added to water, then extracted with ethyl acetate and washed with brine, dried over Na2SO4. After concentrated, the crude product of 2-(5-chloro-2-methoxyphenyl)-4-fluoro-1H-indole (100 mg, yield: 20%) was obtained. MS (M+H)+: 276/278.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentrated

Sources & evidence

ORD record
ord-a918d2833bdd4ee99330845097d2245b
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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