4-Chlorophenylboronic acid → HCID 178522033, compound

HRID 2053195Notes

Reaction equation

HRID 2053195 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-7e5217389a4f40bbbc685dc353528d80
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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