Cesium carbonate → HCID 87461389, compound

HRID 501203Notes

Reaction equation

HRID 501203 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([C:15]4[N:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][N:16]=4)[CH2:14][C:5]=3[C:4]=2[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH:31]([C:33]1[O:37][C:36](B(O)O)=[CH:35][CH:34]=1)=[O:32]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:24][O:23][C:21]([C:18]1[CH:19]=[N:20][C:15]([N:13]2[CH2:12][CH2:11][C:6]3[NH:7][C:8]4[CH:9]=[CH:10][C:2]([C:36]5[O:37][C:33]([CH:31]=[O:32])=[CH:34][CH:35]=5)=[CH:3][C:4]=4[C:5]=3[CH2:14]2)=[N:16][CH:17]=1)=[O:22]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27343555-Formylfuran-2-boronic acidHCID 58703349HCID 58703349, compound

Product 1

HCID 87461389HCID 87461389, compoundYield 46.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of Example 33 (0.25 g, 0.64 mmol) in THF:H20 (4:1) were added Cs2CO3 (1.689 g, 5.16 mmol) and 5-formyl-2-furanboronic acid (0.180 g, 1.29 mmol). The reaction mixture was thoroughly degassed and freshly prepared tetrakis(triphenylphosphine)palladium(0) (0.186 g, 0.16 mmol) was added under nitrogen atmosphere at room temperature. The reaction mixture temperature was raised to 80° C. and continued stirring for 12 hr. The progress of the reaction was monitored by TLC analysis and upon completion of the reaction the THF was removed under reduced pressure. The mixture was partitioned between ethyl acetate (100 mL) and water (15 mL). The organic layer was separated, dried over Na2SO4 filtered and the solvent was removed under reduced pressure to give crude residue, which was purified by column chromatography using silica gel to give methyl-2-{8-[5-(formyl)-2-furyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate (0.12 g, 46.2%)

Workup

  1. customThe reaction mixture was thoroughly degassed
  2. customwas removed under reduced pressure
  3. customThe mixture was partitioned between ethyl acetate (100 mL) and water (15 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customto give crude residue, which
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-049bcba1a9cd444e84aadd9f3487768e
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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