Aluminum(III) Chloride → Methyl 4-{(2rs)-2-[(5-chloro-1h-indol-2-yl)carbonyl]pentyl}benzoate

HRID 1818623Notes

Reaction equation

HRID 1818623 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]([CH:24]([CH2:36][CH2:37][CH3:38])[CH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1)=[O:23])C1C=CC=CC=1>C1C=CC=CC=1>[Cl:21][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[NH:12][C:13]([C:22]([CH:24]([CH2:36][CH2:37][CH3:38])[CH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1)=[O:23])=[CH:14]2

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 67482415Methyl 4-{(2rs)-2-[(1-benzyl-5-chloro-1h-indol-2-yl)carbonyl]pentyl}benzoate

Product 1

HCID 67482179Methyl 4-{(2rs)-2-[(5-chloro-1h-indol-2-yl)carbonyl]pentyl}benzoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To flask containing AlCl3 (1.57 g, 11.7 mmol) was added a solution of the title compound of Example 3 Step C (1.39 g, 2.94 mmol) in benzene (8.0 mL). After 1 h, the reaction mixture was quenched by addition of sat. aq. NH4Cl. The aqueous phase was extracted with EtOAc, and organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 25%, then 25 to 100% EtOAc in hexanes) provided the title compound: LCMS A, tr=4.03 min, m/z 384.3 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 9.29 (s, 1H), 7.94 (d, J=8.5 Hz, 2H), 7.68 (s, 1H), 7.40-7.28 (m, 4H), 7.07 (d, J=1.5 Hz, 1H), 3.92 (s, 3H), 3.63 (dddd, J=8.0, 8.0, 6.0, 6.0 Hz 1H), 3.22 (dd, J=14.0, 8.5 Hz, 1H), 2.93 (dd, J=14.0 Hz, 6.0 Hz, 1 H), 1.92-1.84 (m, 1H), 1.66-1.59 (m, 1H), 1.41-1.34 (m, 2H), 0.93 (t, J=7.5 Hz, 3H).

Workup

  1. customthe reaction mixture was quenched by addition of sat. aq. NH4Cl
  2. extractionThe aqueous phase was extracted with EtOAc, and organic phase
  3. dry with materialwas dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel (0 to 25%

Sources & evidence

ORD record
ord-0a89219f9f97401f88c0262d2480face
Source dataset
uspto-grants-2009_10
Patent number
US07598398B2

Reaction notes

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