1,2-Dichloroethane → HCID 59332769, compound

HRID 656036Notes

Reaction equation

HRID 656036 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([OH:13])=O)[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH:18]([CH3:20])[S:17](=[O:22])(=[O:21])[CH:16]([CH3:23])[CH2:15]1.C(Cl)CCl.C1C=CC2N(O)N=[N:34]C=2C=1.N.O1CCOCC1>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:34])=[O:13])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:15][CH:16]([CH3:23])[S:17](=[O:21])(=[O:22])[CH:18]([CH3:20])[CH2:19]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 312751,4-DioxaneHCID 757711-HydroxybenzotriazoleHCID 59332558HCID 59332558, compound

Product 1

HCID 59332769HCID 59332769, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5-bromo-3-(2,6-dimethyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylic acid (0.187 g, 0.467 mmol) was suspended in DMF (3 mL) with EDC (0.269 g, 1.40 mmol, 3 eq) and HOBt (0.072, 0.467 mmol) in a 10 mL microwave reaction vessel. 0.5M Ammonia in 1,4-dioxane (0.93 mL, 0.467 mmol) was added and heated on the microwave at 100° C. for 20 minutes. The reaction was diluted with water and extracted with Ethyl acetate. The combined organics were washed with 2× water, 2×1N NaOH, brine then dried with magnesium sulfate, to give 0.150 g (80%) of the title compound.

Workup

  1. extractionextracted with Ethyl acetate
  2. washThe combined organics were washed with 2× water, 2×1N NaOH, brine
  3. dry with materialthen dried with magnesium sulfate

Sources & evidence

ORD record
ord-d7eb058e5f1449cea5c90e432391dc1a
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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