Ethyl Acetate → 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(4-formyl-2-thienyl)-1H-indole-7-carboxamide

HRID 562023

Reaction equation

HRID 562023 reaction equation
Br[C:2]1[S:6][CH:5]=[C:4]([CH:7]=[O:8])[CH:3]=1.[CH2:9]([S:11]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[C:28]3[C:23](=[C:24]([C:38]([NH2:40])=[O:39])[CH:25]=[C:26](B4OC(C)(C)C(C)(C)O4)[CH:27]=3)[NH:22][CH:21]=2)[CH2:16][CH2:15]1)(=[O:13])=[O:12])[CH3:10].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO>[CH2:9]([S:11]([N:14]1[CH2:15][CH2:16][CH:17]([C:20]2[C:28]3[C:23](=[C:24]([C:38]([NH2:40])=[O:39])[CH:25]=[C:26]([C:2]4[S:6][CH:5]=[C:4]([CH:7]=[O:8])[CH:3]=4)[CH:27]=3)[NH:22][CH:21]=2)[CH2:18][CH2:19]1)(=[O:13])=[O:12])[CH3:10]

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 122848945-Bromothiophene-3-carbaldehydeHCID 598289293-[1-(ethylsulfonyl)-4-piperidinyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide

Product 1

HCID 577328283-[1-(ethylsulfonyl)-4-piperidinyl]-5-(4-formyl-2-thienyl)-1H-indole-7-carboxamideYield 161.8%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-bromo-3-thiophenecarbaldehyde (250 mg, 1.29 mmol) in dioxane (4.5 mL) and H2O (1.5 mL) was added 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide (200 mg, 0.43 mmol), potassium carbonate (250 mg, 2.58 mmol) and tetrakis(triphenylphosphine)palladium (0) (56 mg, 0.049 mmol). The reaction was run in the microwave at 150° C. for 20 min. It was then treated with EtOAc and H2O to obtain the crude product. This was then treated with MeOH (10 mL) and the solid was filtered and collected to give 310 mg of the desired title compound.

Workup

  1. customto obtain the crude product
  2. filtrationthe solid was filtered
  3. customcollected

Sources & evidence

ORD record
ord-5087085236c24208919a44dfb54a1af7
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Linked notes

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