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Potassium Carbonate → N-[3-(5-Chloro-thiophen-2-yl)-1-isopropyl-1H-indol-6-yl]-methanesulfonamide

HRID 2079886
Notes
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Reaction equation

HRID 2079886 reaction equation
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:11]=2)[C:6](B2OC(C)(C)C(C)(C)O2)=[CH:5]1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[C:34]1[S:35][C:36]([Cl:39])=[CH:37][CH:38]=1.O1CCOCC1>C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[Cl:39][C:36]1[S:35][C:34]([C:6]2[C:7]3[C:12](=[CH:11][C:10]([NH:13][S:14]([CH3:17])(=[O:15])=[O:16])=[CH:9][CH:8]=3)[N:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=2)=[CH:38][CH:37]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 761332-Bromo-5-chlorothiopheneHCID 57442204N-(1-Isopropyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-6-yl)methanesulfonamide

Product 1

HCID 67100553N-[3-(5-Chloro-thiophen-2-yl)-1-isopropyl-1H-indol-6-yl]-methanesulfonamideYield 34.5%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Method J Place N-[1-isopropyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indol-6-yl]-methanesulfonamide (266 mg, 0.70 mmol), potassium carbonate (242 mg, 1.75 mmol), 2-bromo-5-chloro-thiophene (207 mg, 1.05 mmol), dioxane (6 mL) and water (1 mL), followed by addition of tetrakis(triphenylphosphine) palladium (0) (20 mg, 0.018 mmol) in a sealed tube under nitrogen. Heat the reaction mixture at 100° C. overnight, then cool to room temperature. Dilute the reaction mixture with ethyl acetate, and sequentially wash the resulting mixture with water and brine. Dry the organic layer over MgSO4. Chromatograph the crude residue on silica gel column eluting with hexane and ethyl acetate (gradient) to give 89 mg (34%) of the title compound. 1H NMR (CDCl3) δ 7.79 (d, 1H, J=8.8 Hz), 7.42 (d, 1H, J=1.8 Hz), 7.35 (s, 1H), 6.97 (dd, 1H, J=2.0, 8.6 Hz), 6.93 (d, 1H, J=4.0 Hz), 6.88 (d, 1H, J=4.0 Hz), 4.50-4.67 (m, 1H), 2.97 (s, 3H), 1.52 (d, 6H, J=6.6 Hz).

Workup

  1. temperaturecool to room temperature
  2. washsequentially wash the resulting mixture with water and brine
  3. dry with materialDry the organic layer over MgSO4
  4. washChromatograph the crude residue on silica gel column eluting with hexane and ethyl acetate (gradient)

Sources & evidence

ORD record
ord-7e52b2b854af4ecbb6a4195e74e07e71
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07932284B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes