Potassium Carbonate → 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(8-oxo-5,6,7,8-tetrahydro-2-naphthalenyl)-1H-indole-7-carboxamide

HRID 562064

反応式

HRID 562064 の反応式
[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:43]=[C:42]2[C:37]([CH2:38][CH2:39][CH2:40][C:41]2=[O:44])=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>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.[Pd]>[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]=[CH:36][C:37]5[CH2:38][CH2:39][CH2:40][C:41](=[O:44])[C:42]=5[CH:43]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2]

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 2527317-Bromo-1,2,3,4-tetrahydronaphthalen-1-oneHCID 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 667228493-[1-(ethylsulfonyl)-4-piperidinyl]-5-(8-oxo-5,6,7,8-tetrahydro-2-naphthalenyl)-1H-indole-7-carboxamide

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
160 °C

実験手順

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 (200 mg, 0.434 mmol) in dioxane (3.0 mL) and H2O (1.0 mL) was added 7-bromo-3,4-dihydro-1(2H)-naphthalenone (292 mg, 1.30 mmol), and potassium carbonate (360 mg, 2.60 mmol) in a microwave tube. The reaction mixture was degassed for 5 min before the addition of tetrakis (triphenylphosphosphine) palladium (0) (50 mg, 0.043 mmol). The reaction was then heated in the microwave for 30 min at 160° C. The reaction was then filtered and the solid was dissolved in EtOAc and H2O. The organic layer was separated and concentrated. The crude residue was purified by Gilson Preparatory HPLC to yield 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(8-oxo-5,6,7,8-tetrahydro-2-naphthalenyl)-1H-indole-7-carboxamide.

後処理

  1. filtrationThe reaction was then filtered
  2. dissolutionthe solid was dissolved in EtOAc
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. customThe crude residue was purified by Gilson Preparatory HPLC

出典と根拠

ORDレコード
ord-a4a0f07c6b5f4f128cf50b23f35fe1d9
出典データセット
uspto-grants-2011_11
特許番号
US08063071B2

関連ノート

読み込み中…