Acetyl chloride → HCID 59426296, compound

HRID 907133Notes

Reaction equation

HRID 907133 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[N:11]([CH2:23][CH3:24])[C:12]3[C:17]([C:18]=2[C:19]#[N:20])=[CH:16][CH:15]=[C:14]([O:21][CH3:22])[CH:13]=3)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:32](Cl)(=[O:34])[CH3:33]>C1COCC1>[C:19]([C:18]1[C:17]2[C:12](=[CH:13][C:14]([O:21][CH3:22])=[CH:15][CH:16]=2)[N:11]([CH2:23][CH3:24])[C:10]=1[C:9]#[C:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:32](=[O:34])[CH3:33])=[CH:3][CH:4]=1)#[N:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 11587731HCID 11587731, compound

Product 1

HCID 59426296HCID 59426296, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Aminophenylethynyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (95 mg, 0.29 mmol), prepared as described in Example 1H, was dissolved in THF (1.4 mL). Triethylamine (84 μL, 0.6 mmol) was added, followed by dropwise addition of acetyl chloride (44 μL, 0.5 mmol). This was stirred at room temperature for 1 h. The reaction mixture was partitioned between H2O and EtOAc. The organic layer was dried and concentrated. Purification by silica chromatography (9/1, CH2Cl2/EtOAc) yielded N-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-ylethynyl)-phenyl]-acetamide (103 mg, 96%) as a yellow solid.

Workup

  1. customThe reaction mixture was partitioned between H2O and EtOAc
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customPurification by silica chromatography (9/1, CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-e20482268ee44fd0a21064498909273c
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

Loading…