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Cesium carbonate → 2-(1-tert-butoxycarbonyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-(tert-butyl-dimethyl-silanoxy)-indole-1-carboxylic acid tert-butyl ester

HRID 2078684
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HRID 2078684 반응식
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][S:15][C:11]=2[C:10](I)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]([Si:21]([CH3:43])([CH3:42])[O:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[N:28]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:27](B(O)O)=[CH:26]2)([CH3:20])([CH3:19])[CH3:18].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C(OCC)(=O)C>[C:35]([O:34][C:32]([N:28]1[C:29]2[C:25](=[CH:24][C:23]([O:22][Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:42])[CH3:43])=[CH:31][CH:30]=2)[CH:26]=[C:27]1[C:10]1[C:11]2[S:15][CH:14]=[CH:13][C:12]=2[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[N:9]=1)=[O:33])([CH3:38])([CH3:37])[CH3:36]
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참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 222851345-(tert-Butyldimethylsilyloxy)-1H-indole-2-boronic acid, N-BOC protectedHCID 57637299tert-Butyl 3-iodo-1H-thieno[3,2-c]pyrazole-1-carboxylate

생성물 1

HCID 113076212-(1-tert-butoxycarbonyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-(tert-butyl-dimethyl-silanoxy)-indole-1-carboxylic acid tert-butyl ester수율 61%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

실험 절차

To a solution of 3-iodo-thieno[3,2-c]pyrazole-1-carboxylic acid tert-butyl ester (200 mg, 0.57 mmol, Example 5B) and bis-(diphenylphosphinoferrocene)-dichloro palladium (complex with dichloromethane 1:1, 21 mg, 0.03 mmol) in 1,4-dioxane (5 mL) is added 5-(tert-butyl-dimethyl-silanoxy)-1-(tert-butoxycarbonyl)-1H-indole-2-boronic acid (335 mg, 0.86 mmol, prepared as described in Example 4-6 of International Patent Application Publication No. WO 02/32861) followed by a solution of cesium carbonate (741 mg, 2.28 mmol) in water (2 mL). The mixture is stirred at reflux for 15 minutes. Then it is diluted with ethyl acetate and washed with water and brine. The organic layer is dried over magnesium sulfate and concentrated. The residue is chromatographed through silica gel (n-heptane-ethyl acetate, 95:05 as eluant) to afford 200 mg (61%) of 2-(1-tert-butoxycarbonyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-(tert-butyl-dimethyl-silanoxy)-indole-1-carboxylic acid tert-butyl ester as a white foam. LC/MS: RT=4.29 minutes, 570.1 m/e.

후처리

  1. customprepared
  2. temperatureat reflux for 15 minutes
  3. washwashed with water and brine
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is chromatographed through silica gel (n-heptane-ethyl acetate, 95:05 as eluant)

출처 및 근거

ORD 기록
ord-7a067838919c4a6897664850d09921ab
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07928231B2

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