4-Chlorobenzoyl chloride → HCID 86615641, compound

HRID 1435884Notes

Reaction equation

HRID 1435884 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[CH3:15][S:16][C:17]1[C:22]2[CH:23]=[C:24]3[N:29]([C:21]=2[N:20]=[CH:19][CH:18]=1)[CH2:28][CH2:27][CH2:26][CH:25]3[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]>ClCCCl>[CH2:34]([O:33][C:31](=[O:32])[CH2:30][CH:25]1[C:24]2[N:29]([C:21]3[N:20]=[CH:19][CH:18]=[C:17]([S:16][CH3:15])[C:22]=3[C:23]=2[C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:28][CH2:27][CH2:26]1)[CH3:35]

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 86615642HCID 86615642, compound

Product 1

HCID 86615641HCID 86615641, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-chlorobenzoyl chloride (0.30 g, 1.7 mmol) in 1,2-dichloethane (6.0 mL) was added AlCl3 (0.24 g, 1.8 mmole). After a period of 5 min. a solution of ethyl [4-(methylthio)-6,7,8,9-tetrahydropyrido[3,2-b]indolizin-6-yl]acetate from Example 1 Step 8 (0.15 g, 0.47 mmole) in 1,2-dichloroethane (6.0 mL) was added to the previous mixture. After a period of 4 h, at 80° C., the reaction mixture was partitioned between EtOAc and NaHCO3. The organic phase was separated, dried over Na2SO4 and evaporated. The title compound was purified by flash chromatography.

Workup

  1. customat 80° C., the reaction mixture was partitioned between EtOAc and NaHCO3
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe title compound was purified by flash chromatography

Sources & evidence

ORD record
ord-d7133934c5224b6c8ad56c2bc2e86a2a
Source dataset
uspto-grants-2009_11
Patent number
US07618979B2

Reaction notes

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