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Potassium Phosphate, Tribasic → Ethyl 2-[6-{1-[(1,1-dimethylethyl)(dimethyl)silyl]-1H-indol-4-yl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate

HRID 2039706
Notes
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Reaction equation

HRID 2039706 reaction equation
Cl[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:4]([C:20]2[O:21][C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][N:24]=2)[CH:3]=1.[CH3:30][C:31]([Si:34]([CH3:48])([CH3:47])[N:35]1[C:43]2[C:38](=[C:39](B(O)O)[CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36]1)([CH3:33])[CH3:32].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.Cl[Pd]C1C=CC=CC=1C1C=CC=CC=1N(C)C.[C@H]12C[C@H](CC1)CC2PC1C[C@H]2C[C@@H]1CC2>[CH3:33][C:31]([Si:34]([CH3:48])([CH3:47])[N:35]1[C:43]2[C:38](=[C:39]([C:2]3[CH:10]=[C:9]4[C:5]([CH:6]=[N:7][N:8]4[S:11]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)(=[O:13])=[O:12])=[C:4]([C:20]4[O:21][C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][N:24]=4)[CH:3]=3)[CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36]1)([CH3:30])[CH3:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 223523971-(tert-Butyldimethylsilyl)-1H-indole-4-boronic acidHCID 59564714HCID 59564714, compound

Product 1

HCID 59564707Ethyl 2-[6-{1-[(1,1-dimethylethyl)(dimethyl)silyl]-1H-indol-4-yl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylateYield 38.9%

Reagents, catalysts & solvents 3

HCID 178420574
HCID 178420574, compound
Catalyst
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 2-[6-chloro-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate (1.5 g, 3.47 mmol) in 1,4-dioxane (15 ml) and water (1.5 ml) was added {1-[(1,1-dimethylethyl)(dimethyl)silyl]-1H-indol-4-yl}boronic acid (1.243 g, 4.52 mmol, available from Combi-Blocks Inc.), chloro[2′-(dimethylamino)-2-biphenylyl]palladium-1(1R,4S)-bicyclo[2.2.1]hept-2-yl[(1S,4R)-bicyclo[2.2.1]hept-2-yl]phosphane (0.097 g, 0.174 mmol) and potassium phosphate tribasic (2.212 g, 10.42 mmol). The reaction mixture was heated to 100° C. for 3 h, the solvent removed in vacuo and the residue partitioned between dichloromethane (20 ml) and water (10 ml). Saturated sodium chloride solution (100 ml) was added and the organic phase separated and dried over anhydrous sodium sulphate. The crude product was purified by silica gel chromatography, eluting with a gradient of cyclohexane and ethyl acetate. The desired fractions were concentrated to give the title compound as a white solid (0.846 g), which by LCMS contained some unreacted starting material.

Workup

  1. customthe solvent removed in vacuo
  2. customthe residue partitioned between dichloromethane (20 ml) and water (10 ml)
  3. additionSaturated sodium chloride solution (100 ml) was added
  4. customthe organic phase separated
  5. dry with materialdried over anhydrous sodium sulphate
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of cyclohexane and ethyl acetate
  8. concentrationThe desired fractions were concentrated

Sources & evidence

ORD record
ord-70b7761a1f374300ae4d025d50621d47
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08580797B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes