Methanol → HCID 67520578, compound

HRID 1925282Notes

Reaction equation

HRID 1925282 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([O:17][C:18]3[C:27]4C(=C[C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=4)N=CC=3)=[CH:12][CH:13]=2)[CH:8]=1)(=O)=O.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:63][OH:64].CC[N:67]([CH2:70][CH3:71])[CH2:68][CH3:69].CN([CH:75]=[O:76])C>O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:29][O:28][C:25]1[CH:26]=[C:27]2[C:68](=[CH:69][C:24]=1[O:30][CH3:31])[N:67]=[CH:70][CH:71]=[C:18]2[O:17][C:11]1[CH:10]=[C:9]2[C:14]([CH:15]=[CH:16][C:7]([C:63]([O:76][CH3:75])=[O:64])=[CH:8]2)=[CH:13][CH:12]=1

Participants

8

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 86608615HCID 86608615, compound

Product 1

HCID 67520578HCID 67520578, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 7-(6,7-dimethoxyquinolin-4-yloxy)naphthalen-2-yl trifluoromethanesulfonate (Step b, 1.0 g, 2.08 mmol) in DMF (10 mL) in a sealed tube, Pd(OAc)2 (0.094, 0.416 mmol) was added, followed by DPPP (0.257 g, 0.624 mmol). CO(g) was bubbled through the mixture for 5 min, and MeOH (2 mL) and Et3N (0.58 mL, 4.16 mmol) was added. The tube was sealed and the mixture was stirred at 70° C. for 2 h. The reaction was diluted with water and extracted with EtOAc 3×. The combined organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The crude material was taken on directly without purification. MS (ESI, pos. ion) m/z: 390.2 (M+1).

Workup

  1. customCO(g) was bubbled through the mixture for 5 min
  2. customThe tube was sealed
  3. extractionextracted with EtOAc 3×
  4. washThe combined organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customdirectly without purification

Sources & evidence

ORD record
ord-a314000cdb5449b3adb1cc8122fc29bd
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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