1,2-Dichloroethane → HCID 363110, compound

HRID 1063243Notes

Reaction equation

HRID 1063243 reaction equation
[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[C:14](O)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.C(Cl)CCl>CN(C=O)C.O>[C:14]([N:2]1[CH2:3][CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:1]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 107838Tetrahydro-beta-carbolineHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 363110HCID 363110, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (2.0 g. 11.6 mmole) in dry DMF (20 mL) at RT was added benzoic acid (1.56 g, 12.77 mmole), 1-hydroxybenzotriazole hydrate (1.72 g, 12.77 mmole) and diisopropylethylamine (1.65 g, 12.77 mmole). After 10 min, EDC (2.44 g, 12.77 mmole) was added and the reaction was allowed to stir for 12 hr. The reaction contents were poured into H2O (100 mL) and extracted with EtOAc (2×100 mL). The combined organic phases were washed sequentially with H2O and brine, then were dried over Na2SO4. Concentration under reduced pressure and purification on silica (hexanes/EtOAc, 1:1) afforded the title compound (3.0 g. 94%) as a white solid: MS (ES) m/e 277 (M+H)+.

Workup

  1. customThe reaction contents
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic phases were washed sequentially with H2O and brine
  4. dry with materialwere dried over Na2SO4
  5. concentrationConcentration
  6. customunder reduced pressure and purification on silica (hexanes/EtOAc, 1:1)

Sources & evidence

ORD record
ord-6d4e95eceec04940a671db89576f77d6
Source dataset
uspto-grants-2005_11
Patent number
US06964970B2

Reaction notes

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