Anisole → HCID 67482568, compound

HRID 1818633Notes

Reaction equation

HRID 1818633 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C([N:12]1[C:20]2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[CH:14]=[C:13]1[C:22](=[O:46])[CH:23]([CH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]([CH3:45])([CH3:44])[CH3:43])=[CH:38][CH:37]=1)[CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1>C1(C)C=CC=CC=1>[C:42]([C:39]1[CH:38]=[CH:37][C:36]([CH2:35][CH:23]([C:22]([C:13]2[NH:12][C:20]3[C:15]([CH:14]=2)=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=3)=[O:46])[CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:33][CH:34]=2)=[CH:41][CH:40]=1)([CH3:45])([CH3:43])[CH3:44]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 67482775HCID 67482775, compound

Product 1

HCID 67482568HCID 67482568, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) flask containing AlCl3 (622 mg, 4.66 mmol) was added a solution of the title compound of Example 12 Step C (674 mg, 1.17 mmol) and anisole (0.253 mL, 2.33 mmol) in toluene (3 mL). After 30 min, the mixture was removed from the 0° C. bath and allowed to stir at room temperature for 1.5 h, whereupon it was poured into H2O. The aqueous phase was extracted with EtOAc, and the organic phase was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 30%, then 30 to 100% EtOAc in hexanes) provided the title compound: LCMS E, tr=4.50 min, m/z 488.2 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.92 (s, 1H), 7.86 (d, J=8.5 Hz, 2H), 7.57 (s, 1H), 7.29-7.25 (m, 2H), 7.23 (d, J=7.0 Hz, 2H), 7.20 (d, J=8.5 Hz, 2H), 7.08 (d, J=8.0 Hz, 2H), 6.86 (d, J=2.0 Hz, 1H), 3.86-3.81 (m, 1H), 3.85 (s, 3H), 3.20 (dd, J=14.0, 9.0 Hz, 1H), 3.13 (dd, J=14.0, 7.5 Hz, 1H), 2.92 (dd, J=13.5, 5.5 Hz, 1H), 2.83 (dd, J=13.5, 7.0 Hz, 1H), 1.23 (s, 9H).

Workup

  1. customthe mixture was removed from the 0° C. bath
  2. additionwas poured into H2O
  3. extractionThe aqueous phase was extracted with EtOAc
  4. concentrationthe organic phase was concentrated in vacuo
  5. customPurification by flash chromatography on silica gel (0 to 30%

Sources & evidence

ORD record
ord-e719655a6e014890bbf2c73e0e6fdb04
Source dataset
uspto-grants-2009_10
Patent number
US07598398B2

Reaction notes

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