Ethyl Acetate → HCID 66723228, compound

HRID 562218Notes

Reaction equation

HRID 562218 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:30]([NH2:32])=[O:31])[CH:17]=[C:18](B4OC(C)(C)C(C)(C)O4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].Br[C:34]1[CH:35]=[C:36]([C:39](=[O:41])[CH3:40])[S:37][CH:38]=1.[C:42](=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>[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:30]([NH2:32])=[O:31])[CH:17]=[C:18]([C:34]4[CH:35]=[C:36]([C:39](=[O:41])[CH2:40][CH3:42])[S:37][CH:38]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:4])=[O:5])[CH3:2]

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27352371-(4-Bromo-2-thienyl)ethan-1-oneHCID 598289293-[1-(ethylsulfonyl)-4-piperidinyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide

Product 1

HCID 66723228HCID 66723228, compoundYield 77%

Reagents, catalysts & solvents 4

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

Procedure

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide (300 mg, 0.65 mmol) in dioxane (9 mL) and H2O (3 mL) was added 1-(4-bromo-2-thienyl)ethanone (400 mg, 1.95 mmol), potassium carbonate (538 mg, 3.90 mmol), and tetrakis(triphenylphosphine)palladium(0) (70 mg, 0.060 mmol). The reaction was run in the microwave at 150° C. for 20 min. An aqueous work-up was performed using EtOAc and H2O followed by addition of MeOH (3 mL) to the crude product. The desired product precipitated and was filtered to give 230 mg of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-propanoyl-3-thienyl)-1H-indole-7-carboxamide (77%).

Workup

  1. customThe desired product precipitated
  2. filtrationwas filtered

Sources & evidence

ORD record
ord-abd242c359a044c0a29c7427e7e63357
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Reaction notes

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