Water → 2-(7-fluoro-4-methoxy-1-methyl-5-phenyl-1H-indol-3-yl)-N,N-dimethylacetamide

HRID 1404092Notes

Reaction equation

HRID 1404092 reaction equation
Br[C:2]1[C:3]([O:19][CH3:20])=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([CH3:12])[CH:6]=[C:5]2[CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:11][C:9]1[CH:10]=[C:2]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:3]([O:19][CH3:20])=[C:4]2[C:8]=1[N:7]([CH3:12])[CH:6]=[C:5]2[CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 669270242-(5-bromo-7-fluoro-4-methoxy-1-methyl-1H-indol-3-yl)-N,N-dimethylacetamide

Product 1

HCID 669270952-(7-fluoro-4-methoxy-1-methyl-5-phenyl-1H-indol-3-yl)-N,N-dimethylacetamideYield 81%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To the solution of 8-11 (200 mg, 0.58 mmol) in dioxane (10 mL) was added phenylboronic acid (86 mg, 0.70 mmol), Pd(PPh3)4 (68 mg, 0.06 mmol), and Cs2CO3 (760 mg, 2.3 mmol) under nitrogen atmosphere. The reaction mixture was refluxed overnight, poured into water and extracted with ethyl acetate (20 mL×3). The separated organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (elution with petroleum ether:ethyl acetate=1:1) to afford 8-12 (160 mg, 81%) as white solid. LCMS: calc 340.4 and found 341.1 [MH]+.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. extractionextracted with ethyl acetate (20 mL×3)
  3. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (elution with petroleum ether:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-f4d3c79341bf4e27ab4bea91d571ed04
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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