4-Chlorophenylboronic acid → HCID 178522033, compound

HRID 1444291Notes

Reaction equation

HRID 1444291 reaction equation
[NH:1]1[C:5]([CH2:6][C:7]2[CH:8]=[C:9]([NH:13][C:14]([C:16]3[O:17][C:18](Br)=[CH:19][CH:20]=3)=[O:15])[CH:10]=[CH:11][CH:12]=2)=[N:4][N:3]=[N:2]1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>>[NH:1]1[C:5]([CH2:6][C:7]2[CH:8]=[C:9]([NH:13][C:14]([C:16]3[O:17][C:18]([C:26]4[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=4)=[CH:19][CH:20]=3)=[O:15])[CH:10]=[CH:11][CH:12]=2)=[N:4][N:3]=[N:2]1

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 178522031HCID 178522031, compound

Product 1

HCID 178522033HCID 178522033, compound

Procedure

The bromo-derivative (84) (100 mg, 0.29 mmol) was coupled to 4-chloro-phenylboronic acid (49 mg, 0.32 mmol) using Method E. After reaction, the solvents were removed under a stream of N2, and the residue was dissolved in saturated NaHCO3 solution (5 ml) and washed with EtOAc (5 ml). The aqueous layer was acidified to pH 1 with 2M HCl until a white precipitate formed and extracted with EtOAc (2×5 ml). The organic layer was dried (MgSO4), filtered and the solvent removed in vacuo. The residue was triturated with MeCN (4 ml) and further purified by preparative HPLC to give the title compound.

Workup

  1. customAfter reaction
  2. customthe solvents were removed under a stream of N2
  3. dissolutionthe residue was dissolved in saturated NaHCO3 solution (5 ml)
  4. washwashed with EtOAc (5 ml)
  5. customformed
  6. extractionextracted with EtOAc (2×5 ml)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed in vacuo
  10. customThe residue was triturated with MeCN (4 ml)
  11. customfurther purified by preparative HPLC

Sources & evidence

ORD record
ord-eb92b8c999a14c60b9fde71d762baa28
Source dataset
uspto-grants-2010_02
Patent number
US07662839B2

Reaction notes

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