Cesium carbonate → HCID 58703310, compound

HRID 501200Notes

Reaction equation

HRID 501200 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[CH:38]=[CH: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:17]=[N:16][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[CH:37]=[CH:38][C:33]([CH:31]=[O:32])=[CH:34][CH:35]=5)=[CH:3][C:4]=4[C:5]=3[CH2:14]2)=[N:20][CH:19]=1)=[O:22]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 5910734-Formylphenylboronic AcidHCID 58703349HCID 58703349, compound

Product 1

HCID 58703310HCID 58703310, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a 0° C. solution of Example 33 (1.5 g, 3.37 mmol) in THF:H20 (4:1) were added Cs2CO3 (10.07 g, 30.99 mmol) and 4-formylphenylboronic acid (1.158 g, 7.75 mmol). The reaction mixture was thoroughly degassed and freshly prepared tetrakis(triphenylphosphine)palladium(0) (1.119 g, 0.96 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 Example 102 (1.0, 62.6%). 1HNMR (CDCl3, 200 MHz) δ: 10.11 (s, 1H), 8.90 (s, 2H), 8.17 (s, 1H), 8.00-7.92 (m, 2H), 7.85-7.80 (m, 2H), 7.64-7.38 (m, 4H), 5.15 (s, 2H), 4.39 (t, 2H, J=5.4 Hz), 3.88 (s, 3H), 2.98 (t, 2H, J=5.4 Hz); m/e=413(M+1).

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
  10. customto provide Example 102 (1.0, 62.6%)

Sources & evidence

ORD record
ord-7735b35a35244b90a47283676e779e2a
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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