2,6-Dimethylphenol → HCID 58914735, compound

HRID 1297758Notes

Reaction equation

HRID 1297758 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:6](=[O:19])[C:5]2=O.[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:23]=1[OH:29].[C:30]([O-:33])(O)=O.[Na+]>FC(F)(F)S(O)(=O)=O.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:6](=[O:19])[C:5]2([C:2]1[CH:3]=[C:4]([CH3:5])[C:30]([OH:33])=[C:9]([CH3:8])[CH:10]=1)[C:26]1[CH:25]=[C:24]([CH3:28])[C:23]([OH:29])=[C:22]([CH3:21])[CH:27]=1

Participants

6

Reactant 3

HCID 113352,6-DimethylphenolHCID 516892Sodium BicarbonateHCID 2196908HCID 2196908, compound

Product 1

HCID 58914735HCID 58914735, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

Combine crude 5-bromo-1-(2-chloro-benzyl)-1H-indole-2,3-dione (72 mg, 0.21 mmol) with 2,6-dimethylphenol (200 mg, 1.64 mmol) in trifluoromethanesulfonic acid (1 mL) and stir for 1 h. Dilute with CH2Cl2 and stir with ice water for 20 min. Pipette off ice water and stir with saturated NaHCO3 solution for 20 min. Remove aqueous by pipette and pass organic layer through a 5 mL Varian Chem Elut column. Concentrate in vacuo to give 131 mg solid. Triturate in MeOH to give 50 mg (41%) of a white solid. MS (ES): m/z=576, 578 (M+1), 574, 576 (M−1); 1H NMR(DMSO-d6): δ8.31 (s, 2H), 7.53 (d, J=7.9 Hz, 1H), 7.45 (m, 2H), 7.34 (t, J=7.6 Hz, 1H), 7.25 (t, J=7.6 Hz, 1H), 6.95 (m, 2H), 6.71 (s, 4H), 5.06 (s, 2H), 2.09 (s, 12H).

Workup

  1. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-9793b21850b64a65aa14aa15743c8180
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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