Dimethylformamide → HCID 46944831, compound

HRID 1009569Notes

Reaction equation

HRID 1009569 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 occurred. 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-7052d0243310448880c12734cf5422a2
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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