Cesium carbonate → HCID 86607547, compound

HRID 501218Notes

Reaction equation

HRID 501218 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:24][CH2:23][C:14]3[NH:15][C:16]4[CH:17]=[C:18](Br)[CH:19]=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:9][CH:10]=1)=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].[CH:31]([C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=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>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:24][CH2:23][C:14]3[NH:15][C:16]4[CH:17]=[C:18]([C:37]5[CH:36]=[CH:35][CH:34]=[C:33]([CH:31]=[O:32])[CH:38]=5)[CH:19]=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:9][CH:10]=1)=[O:4]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27343563-Formylphenylboronic acidHCID 68464427HCID 68464427, compound

Product 1

HCID 86607547HCID 86607547, compoundYield 39.13%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of methyl-2-(7-bromo-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)pyrimidine-5-carboxylate (0.360 g, 0.93 mmol) in THF:H20 (4:1) were added Cs2CO3 (2.42 g, 7.44 mmol) and 3-formylphenylboronic acid (0.27 g, 1.86 mmol). The reaction mixture was thoroughly degassed and freshly prepared tetrakis(triphenylphosphine)palladium(0) (0.268 g, 0.23 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 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 provide methyl-2-{7-[3-(formyl)phenyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate (0.15 g, 39.13%).

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-b7ff644927ab4087857f3d9782a010af
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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