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

HRID 562023

反応式

HRID 562023 の反応式
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]

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-5087085236c24208919a44dfb54a1af7
出典データセット
uspto-grants-2011_11
特許番号
US08063071B2

関連ノート

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