1,2-Dichloroethane → HCID 22561956, compound

HRID 982992Notes

Reaction equation

HRID 982992 reaction equation
[CH3:1][NH:2][CH3:3].[NH:4]1[C:12]2[C:7](=[C:8]([C:13]3[CH:14]=[C:15]([CH2:19][C:20]([OH:22])=O)[CH:16]=[CH:17][CH:18]=3)[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[NH:4]1[C:12]2[C:7](=[C:8]([C:13]3[CH:14]=[C:15]([CH2:19][C:20]([N:2]([CH3:3])[CH3:1])=[O:22])[CH:16]=[CH:17][CH:18]=3)[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 22561865HCID 22561865, compound

Product 1

HCID 22561956HCID 22561956, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dimethylamine (2M in THF, 5 mL) was added to a mixture of [3-(1H-indol-4-yl)-phenyl]-acetic acid (1.26 g, 5 mmol), EDC (1.19 g, 1.25 eq.) and HOBt (675 mg, 1 eq.) in THF (10 mL) was stirred at rt for 5 hours. The reaction was concentrated, diluted with ethyl acetate, washed with 10% Na2CO3 (3×), brine, dried and concentrated. The residue was purified on a silica gel column to give 658 mg of 2-[3-(1H-indol-4-yl)-phenyl]-N,N-dimethyl-acetamide as a solid.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with 10% Na2CO3 (3×), brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-c81410dd5f9840d798914033df07cd3d
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

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