Acetyl chloride → HCID 59426209, compound

HRID 1009595Notes

Reaction equation

HRID 1009595 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH2:24][CH3:25])[C:13]3[C:18]([C:19]=2[C:20]#[N:21])=[CH:17][CH:16]=[C:15]([O:22][CH3:23])[CH:14]=3)=[CH:7][CH:6]=1.CCN(CC)CC.[C:33](Cl)(=[O:35])[CH3:34]>C1COCC1>[C:20]([C:19]1[C:18]2[C:13](=[CH:14][C:15]([O:22][CH3:23])=[CH:16][CH:17]=2)[N:12]([CH2:24][CH3:25])[C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:1][C:33](=[O:35])[CH3:34])=[CH:6][CH:7]=1)#[N:21]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 59425830HCID 59425830, compound

Product 1

HCID 59426209HCID 59426209, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[4-(2-Aminoethoxy)phenyl]-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (30 mg, 0.09 mmol), prepared as in example 1BB, step B, is dissolved in THF (400 μL), and Et3N (24 μL, 0.17 mmol). Acetyl chloride (10 μL, 0.14 mmol) is added, and the reaction mixture is stirred at room temperature for 2 h. The reaction mixture is partitioned between EtOAc and H2O. The organic layer is dried and concentrated. Purification by silica gel chromatography (EtOAc) yields N-{2-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)phenoxy]ethyl}acetamide (33 mg, 97%) as a white solid.

Workup

  1. customThe reaction mixture is partitioned between EtOAc and H2O
  2. customThe organic layer is dried
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (EtOAc)

Sources & evidence

ORD record
ord-433ee79377f34c7296c26743c0fc6089
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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