Cesium carbonate → HCID 131727416, compound

HRID 2078736Notes

Reaction equation

HRID 2078736 reaction equation
[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[C:12](B(O)O)[NH:13]2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[C:21]([O:25][C:26]([N:28]1[C:32]2[CH:33]=[C:34]([C:36]([CH3:44])([CH3:43])[O:37][SiH2:38][C:39]([CH3:42])([CH3:41])[CH3:40])[S:35][C:31]=2[C:30](I)=[N:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].[C:46](=[O:49])([O-])[O-:47].[Cs+].[Cs+]>O1CCOCC1.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]>[C:1]([O:47][C:46]([N:13]1[C:14]2[C:10](=[CH:9][CH:8]=[C:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:20])[CH3:19])[CH:15]=2)[CH:11]=[C:12]1[C:30]1[C:31]2[S:35][C:34]([C:36]([CH3:44])([CH3:43])[O:37][SiH2:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:33][C:32]=2[N:28]([C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])[N:29]=1)=[O:49])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 67097558HCID 67097558, compoundHCID 131727415HCID 131727415, compound2×

Product 1

HCID 131727416HCID 131727416, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-(tert-butyl-dimethyl-silanoxy)-1H-indole-2-boronic acid [3.57 g, 9.13 mmol, Intermediate (74), prepared by the application of method described in Example 4-6 of International Patent Application Publication No. WO 02/32861] and 5-(tert-butyl-dimethyl-silanyloxymethyl)-3-iodo-thieno[3,2-c]pyrazole-1-carboxylic acid tert-butyl ester [3.47 g, 7.02 mmol, Intermediate (73)] in solution in 1,4-dioxane (60 mL) was added [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (complex with dichloromethane (1:1)) (385 mg, 0.53 mmol). An aqueous solution (25 mL) of cesium carbonate (9.14 g, 28.08 mmol) was added. The mixture was stirred at 80° C. for 1 hour. It was allowed to cool down to room temperature, and was extracted three times with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated. The residue was chromatographed through silica gel (n-heptane/ethyl acetate, 95/05 then 90/10) to produce 2-[1-tert-butoxycarbonyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-1H-thieno[3,2-c]pyrazol-3-yl]-6-(tert-butyl-dimethyl-silanyloxy)-indole-1-carboxylic acid tert-butyl ester [3.8 g, 76%, Intermediate (75)]. LC/MS: 714.38 (M+H), RT=3.27 minutes.

Workup

  1. temperatureto cool down to room temperature
  2. extractionwas extracted three times with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed through silica gel (n-heptane/ethyl acetate, 95/05

Sources & evidence

ORD record
ord-67579b8933724eca8525a2376e317b8d
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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