Dimethylformamide → HCID 46944831, compound

HRID 502158Notes

Reaction equation

HRID 502158 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]([CH2:14][CH3:15])[C:4]=1[C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1)#[N:2].CN(C=O)C.C(Cl)(=O)C(Cl)=O.[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>C(Cl)Cl>[CH2:14]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=2)[C:3]([C:1]#[N:2])=[C:4]1[C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[O:21])=[CH:18][CH:17]=1)[CH3:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8083MorpholineHCID 65578Oxalyl chlorideHCID 66865449HCID 66865449, compound

Product 1

HCID 46944831HCID 46944831, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-benzoic acid (50 mg, 0.16 mmol) is suspended in CH2Cl2 (2.2 mL) and catalytic DMF (2 μL). Oxalyl chloride (22 μL, 0.25 mmol) is added. The reaction mixture is stirred at room temperature for 1 hour, at which time full dissolution occurs. This reaction mixture is pipetted dropwise into a vigorously stirring solution of morpholine (1.0 mL) in CH2Cl2 (5 ml). After addition is complete, the reaction mixture is washed with aqueous HCl solution. The organic layer is dried and concentrated. Purification by silica column (1:1 CH2Cl2/EtOAc) yields 1-ethyl-6-methoxy-2-[4-(morpholine-4-carbonyl)-phenyl]-1H-indole-3-carbonitrile (56 mg, 90%) as a white solid.

Workup

  1. additionAfter addition
  2. washthe reaction mixture is washed with aqueous HCl solution
  3. customThe organic layer is dried
  4. concentrationconcentrated
  5. customPurification by silica column (1:1 CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-64b19738ead2484d8d6dce931b4aa200
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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