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

HRID 562023

반응식

HRID 562023 반응식
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]

참가 물질

9

반응물 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

생성물 1

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

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-5087085236c24208919a44dfb54a1af7
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063071B2

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