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1,2-Dichloroethane → 5-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxamide

HRID 387271
Notes
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Reaction equation

HRID 387271 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11](O)=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][CH2:17][S:16](=[O:21])(=[O:20])[CH2:15]1.C(Cl)CCl.C1C=CC2N(O)N=[N:32]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]([NH2:32])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][CH2:17][S:16](=[O:21])(=[O:20])[CH2:15]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 312751,4-DioxaneHCID 757711-HydroxybenzotriazoleHCID 593327875-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylic acid

Product 1

HCID 593327915-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxamide
Yield 87.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylic acid (0.185 g, 0.497 mmol) was suspended in DMF (2 mL) with EDC (0.286 g, 1.49 mmol, 3 eq) and HOBt (0.076, 0.497 mmol) in a 10 mL microwave reaction vessel. 0.5M ammonia in 1,4-dioxane (1.9 mL, 0.9945 mmol, 2 eq) was added and heated on the microwave at 100° C. for 20 minutes. Reaction was diluted with water and extracted with ethyl acetate. The combined organics were washed with 1N NaOH, water, and brine then dried with magnesium sulfate, to give 0.161 g (87%) of the title compound.

Workup

  1. customReaction
  2. extractionextracted with ethyl acetate
  3. washThe combined organics were washed with 1N NaOH, water, and brine
  4. dry with materialthen dried with magnesium sulfate

Sources & evidence

ORD record
ord-ca0be17611ce4a83bc32366df2ecf4dc
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08372875B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes