Anisole → HCID 42597215, compound

HRID 409384Notes

Reaction equation

HRID 409384 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]2[N:6](CC3C=CC(OC)=CC=3)[C:7](=[O:26])[CH:8]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.C1(OC)C=CC=CC=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClC(Cl)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:37]=[CH:36][C:5]2[NH:6][C:7](=[O:26])[CH:8]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 66741758HCID 66741758, compound

Product 1

HCID 42597215HCID 42597215, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

7-Chloro-5-(4-fluorophenyl)-1-(4-methoxybenzyl)-3-(2-methylbenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (44 mg, 0.086 mmol) was dissolved in dichloroethane (1 mL) under nitrogen and 200 L of anisole was added followed by AlCl3 (69 mg, 0.515 mmol). This mixture was heated to 85° C. for 2.5 h then allowed to cool and diluted with ethyl acetate and ice. This biphasic mixture was stirred vigorously for 20 min, then partitioned, and the organic layer was washed with water twice, then brine once. The aqueous layers were back-extracted once with ethyl acetate, and the combined organic extracts dried over MgSO4. Chromatography on silica gel (5%-30%-40%-50% ethyl acetate in hexanes) provided the title compound (27 mg, 80%) as a yellow solid. APCI MS m/z 415.1 [M+Na+], 393.1 [M+H+]; 1H NMR (300 MHz, CDCl3) δ 9.28 (s, 1H), 7.61-7.16 (m, 11H), 3.91 (t, J=7 Hz, 1H), 3.72-3.69 (m, 2H), 2.50 (s, 3H).

Workup

  1. temperatureto cool
  2. custompartitioned
  3. washthe organic layer was washed with water twice
  4. extractionThe aqueous layers were back-extracted once with ethyl acetate
  5. dry with materialthe combined organic extracts dried over MgSO4

Sources & evidence

ORD record
ord-7a45c7084aa44e7895f8edf80cfb7bab
Source dataset
uspto-grants-2014_06
Patent number
US08759340B2

Reaction notes

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