Dimethylformamide → HCID 46944831, compound

HRID 907139Notes

Reaction equation

HRID 907139 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) was suspended in CH2Cl2 (2.2 mL) and catalytic DMF (2 μL). Oxalyl chloride (22 μL, 0.25 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour, at which time full dissolution occurred. This reaction mixture was pipetted dropwise into a vigorously stirring solution of morpholine (1.0 mL) in CH2Cl2 (5 ml). After addition was complete, the reaction mixture was washed with aqueous HCl solution. The organic layer was dried and concentrated. Purification by silica column (1:1 CH2Cl2/EtOAc) yielded 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 was washed with aqueous HCl solution
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customPurification by silica column (1:1 CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-1d79725d1f754cccafd39161b9cea4be
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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