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Potassium Carbonate → 5-[6-(Dimethylamino)-3-pyridinyl]-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide

HRID 656082
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HRID 656082 반응식
[CH3:1][N:2]([CH3:12])[C:3]1[N:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:14]1[CH:15]=[C:16]2[C:20](=[C:21]([C:23]([NH2:25])=[O:24])[CH:22]=1)[NH:19][CH:18]=[C:17]2[CH:26]1[CH2:31][CH2:30][S:29](=[O:33])(=[O:32])[CH2:28][CH2:27]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[CH3:1][N:2]([CH3:12])[C:3]1[N:8]=[CH:7][C:6]([C:14]2[CH:15]=[C:16]3[C:20](=[C:21]([C:23]([NH2:25])=[O:24])[CH:22]=2)[NH:19][CH:18]=[C:17]3[CH:26]2[CH2:27][CH2:28][S:29](=[O:32])(=[O:33])[CH2:30][CH2:31]2)=[CH:5][CH:4]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 27632716-(Dimethylamino)pyridine-3-boronic acidHCID 593327575-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide

생성물 1

HCID 593327015-[6-(Dimethylamino)-3-pyridinyl]-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide수율 34.8%

시약·촉매·용매 1

HCID 21886435
1,4-Dioxane--water (1/1)
용매

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온도
150 °C

실험 절차

[6-(Dimethylamino)-3-pyridinyl]boronic acid (34 mg, 0.202 mmol), 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (75 mg, 0.202 mmol) and potassium carbonate (84 mg, 0.606 mmol) were suspended in 4 mL of dioxane:water (3:1) and degassed for a few minutes with nitrogen gas. Pd(PPh3)4 (23 mg) was then added and the reaction mixture was heated in a microwave oven at 150° C. for 40 minutes on ‘high’ absorption setting. After heating, LCMS of all crude reaction mixtures showed the desired m/z with few impurities. The crude reaction mixtures were filtered through 500 mg Stratospheres SPE Thiol cartridges eluting with 10 mL methanol/DCM (1:1) and concentrated. The residues were dissolved in DMSO (˜3 mL) and purified via RP-HPLC using an XBridge Prep C18 column with water/acetonitrile (0.1% NH4OH buffer). The desired fractions were concentrated, giving 0.029 g (34.8%) of the title compound.

후처리

  1. customdegassed for a few minutes with nitrogen gas
  2. additionPd(PPh3)4 (23 mg) was then added
  3. customabsorption
  4. temperatureAfter heating
  5. customLCMS of all crude reaction mixtures
  6. customThe crude reaction mixtures
  7. filtrationwere filtered through 500 mg Stratospheres SPE Thiol cartridges
  8. washeluting with 10 mL methanol/DCM (1:1)
  9. concentrationconcentrated
  10. dissolutionThe residues were dissolved in DMSO (˜3 mL)
  11. custompurified via RP-HPLC
  12. concentrationThe desired fractions were concentrated

출처 및 근거

ORD 기록
ord-dd9f812407de4c0f95bbf91ca5ec64b0
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08071584B2

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