1,2-Dichloroethane → HCID 69758887, compound

HRID 1883656Notes

Reaction equation

HRID 1883656 reaction equation
[CH:1]([N:4](C(C)C)[CH2:5]C)(C)C.[CH:10]1[CH:11]=[CH:12][C:13]2N(O)N=[N:16][C:14]=2[CH:15]=1.[CH3:20][N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[C:22]1CNC.C(Cl)CCl.[CH3:37][N:38]([CH:40]=[O:41])[CH3:39]>>[NH2:16][C:14]1[CH:15]=[CH:10][C:11]([C:40]([N:38]([CH3:39])[CH2:37][C:22]2[N:21]([CH3:20])[C:29]3[C:24]([CH:23]=2)=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:41])=[CH:12][C:13]=1[CH2:1][NH:4][CH3:5]

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amine

Product 1

HCID 69758887HCID 69758887, compoundYield 92%

Procedure

To a stirred solution of 4-nitro-3-{[(N-methyl(phenylmethoxy)carbonylamino]methyl}benzoic acid (4.56 g, 13.26 mmole) in DMF (20 mL) at RT was added diisopropylethyl amine (2.31 mL, 13.26 mmole), HOBt (1.79 g, 13.26 mmole), 1-methyl-2-(methylaminomethyl)indole (2.1 g, 12.0 mmole) and finally EDC (2.54 g, 13.26 mmole). After 12 hr, the reaction contents were poured onto H2O (100 mL) and extracted with EtOAc (2×100 mL). The organic phases were combined and sequentially washed with H2O (100 mL) and brine. Drying over Na2SO4 and purification on silica (hexanes/EtOAc, 1:1) afforded the title compound (5.52 g, 92%) as a viscous yellow oil: MS (ES) m/e 501 (M+H)+.

Workup

  1. customthe reaction contents
  2. additionwere poured onto H2O (100 mL)
  3. extractionextracted with EtOAc (2×100 mL)
  4. washsequentially washed with H2O (100 mL) and brine
  5. dry with materialDrying over Na2SO4 and purification on silica (hexanes/EtOAc, 1:1)

Sources & evidence

ORD record
ord-34e7e79401e540e89b04939538af72c1
Source dataset
uspto-grants-2004_07
Patent number
US06762201B1

Reaction notes

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