Skatole → HCID 9794477, compound

HRID 1871023Notes

Reaction equation

HRID 1871023 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[CH3:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH3:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH3:9])=[CH:11]1

Participants

7

Reactant 4

HCID 6736SkatoleHCID 72362-BromotolueneHCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphine

Product 1

HCID 9794477HCID 9794477, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Procedure

The above general procedure was followed using 2-bromotoluene (205 mg, 1.20 mmol), 3-methylindole (131 mg, 1.00 mmol), 3 mo % Pd(dba)2, 2.4 mol % tri-t-butylphosphine, and cesium carbonate (1.70 mmol) in 1.0 mL of toluene. After 12 hours at 100° C., the reaction mixture was adsorbed onto silica gel and chromatographed with 5% ethyl acetate/hexanes to give 195 mg (88%) of N-(2-methylphenyl)-3-methylindole. 1H NMR (300 MHz, CDCl3) δ 7.76 (m, 1H), 7.46 (m, 2H), 7.40 (m, 2H), 7.28 (m, 2H), 7.15 (m, 1H), 7.06 (s, 1H), 2.53 (S, 3H), 2.21 (s, 3H). 13C NMR (76 MHz, CDCl3) δ 138.4, 137.1, 135.7, 131.1, 128.6, 128.1, 127.8, 126.6, 126.2, 121.9, 119.3, 118.9, 111.6, 110.4, 17.7, 9.6.

Workup

  1. customchromatographed with 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-fb4be04fd7df47f8bd9830e02d532980
Source dataset
uspto-grants-2000_08
Patent number
US06100398

Reaction notes

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