Benzoyl chloride, 3-chloro- → 5-(3-chlorobenzoyl)-1-(2-chlorophenyl)-2-(4-methoxyphenyl)4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

HRID 1790033Notes

Reaction equation

HRID 1790033 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[CH2:15][CH2:14][NH:13][CH2:12][C:11]=2[CH:10]=[C:9]1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.[Cl:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](Cl)=[O:30]>ClCCl>[Cl:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29]([N:13]1[CH2:14][CH2:15][C:16]2[N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:9]([C:17]3[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)=[CH:10][C:11]=2[CH2:12]1)=[O:30]

Participants

4

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 220385001-(2-chlorophenyl)-2-(4-methoxyphenyl)4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 220385375-(3-chlorobenzoyl)-1-(2-chlorophenyl)-2-(4-methoxyphenyl)4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridineYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an 8-mL vial charged with piperidinomethyl polystyrene (3.57 mmol/g, 198.4 mg, 0.708 mmol) and a solution of 1-(2-chlorophenyl)-2-(4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine (Example 2, 80.0 mg, 0.236 mmol) in 3 mL dichloromethane was added 3-chlorobenzoyl chloride (62.0 mg, 0.0.54 mmol). The reaction mixture was mixed by orbital shaking for 3 h. The solid was removed by filtration. The filtrate was evaporated, and the residue was purified on silica gel eluting with 1:5 EtOAc/hexanes to give a solid (83.2 mg, 74%): Rf=0.19 (1:2 EtOAc/hexanes).

Workup

  1. additionThe reaction mixture was mixed
  2. customThe solid was removed by filtration
  3. customThe filtrate was evaporated
  4. customthe residue was purified on silica gel eluting with 1:5 EtOAc/hexanes

Sources & evidence

ORD record
ord-6799d787040d4ac2895b8f40a6daa6ba
Source dataset
uspto-grants-2006_07
Patent number
US07071207B2

Reaction notes

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