Potassium Carbonate → 3-(1,1-Dioxidotetrahydro-2H-thiopyran-3-yl)-5-(4-fluorophenyl)-1H-indole-7-carboxamide

HRID 387370노트

반응식

HRID 387370 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][CH2:17][S:16](=[O:21])(=[O:20])[CH2:15]1.[F:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:20]=[S:16]1(=[O:21])[CH2:17][CH2:18][CH2:19][CH:14]([C:5]2[C:4]3[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=[C:2]([C:26]4[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=4)[CH:3]=3)[NH:7][CH:6]=2)[CH2:15]1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 593327915-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxamide

생성물 1

HCID 593326913-(1,1-Dioxidotetrahydro-2H-thiopyran-3-yl)-5-(4-fluorophenyl)-1H-indole-7-carboxamide수율 30.9%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

5-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxamide (0.050 g, 0.134 mmol) and (4-fluorophenyl)boronic acid (0.024 g, 0.174 mmol) was dissolved in a 6:1 solution of 1,4 dioxane (3 mL)/water (0.5 mL) in a 20 mL microwave reaction vessel. Potassium carbonate (0.093 g, 0.670 mmol) was added and the solution was degassed with Nitrogen. PdCl2(dppf)2 (0.017 g, 0.023 mmol) was added and the reaction was heated in a microwave at 100° C. for 20 min. The solution was passed through a StratoSphere SPE PL-Thiol MP SPE column to remove palladium and purified on Gilson preparative HPLC using Acetonitrile/Water with 0.1% TFA. The desired fractions were concentrated, giving 0.016 g (30%) of the title compound.

후처리

  1. customthe solution was degassed with Nitrogen
  2. customto remove palladium
  3. custompurified on Gilson preparative HPLC
  4. concentrationThe desired fractions were concentrated

출처 및 근거

ORD 기록
ord-d9f39e3600ba46dfbde4243e44da0b15
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372875B2

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