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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
ノート
印刷プレビュー

反応式

HRID 656082 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

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

反応条件

温度
150 °C

実験手順

[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.

後処理

  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

出典と根拠

ORDレコード
ord-dd9f812407de4c0f95bbf91ca5ec64b0
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08071584B2

反応ノート

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