Cesium carbonate → HCID 59756932, compound

HRID 1880579Notes

Reaction equation

HRID 1880579 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([Cl:12])[N:3]=1.[OH:13][CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([O-:21])=[O:20])=[CH:17][CH:16]=1.[C:24](=O)([O-])[O-].[Cs+].[Cs+].C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[Cl:12][C:4]1[N:3]=[C:2]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:24])=[O:20])=[CH:22][CH:23]=2)[C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 2986251,3-DichloroisoquinolineHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 7009454HCID 7009454, compound

Product 1

HCID 59756932HCID 59756932, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

A toluene (3 mL) solution containing 1,3-dichloroisoquinoline (50 mg, 0.25 mmol), 4-(hydroxymethyl)benzoate (105 mg, 0.63 mmol), cesium carbonate (206 mg, 0.63 mmol), palladium acetate (5 mg, 0.02 mmol) and racemic-2-(di-t-butylphosphino)-1,1′-binaphthyl (14 mg, 0.035 mmol) was heated at 75° C. for 1.5 hours. The solution was partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over MgSO4. The solution was filtered, concentrated and the residue purified by silica gel chromatography using hexanes/ethyl acetate gradient. 1H NMR (500 MHz, CDCl3): δ 8.30 (d, J=8.3 Hz, 1H); 8.13 (d, J=8.3 Hz, 2H); 7.72-7.70 (m, 2H); 7.65 (d, J=8.2 Hz, 2H); 7.59-7.55 (m, 1H); 7.34 (s, 1H); 5.68 (s, 2H); 3.98 (s, 3H). LCMS2 2.73 min. (M+H)=328

Workup

  1. customThe solution was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated
  6. customthe residue purified by silica gel chromatography
  7. customLCMS2 2.73 min. (M+H)=328

Sources & evidence

ORD record
ord-b057d5aad7ce454c86d78b68931e1a80
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

Loading…