4-Fluorophenylboronic acid → HCID 178522034, compound

HRID 2053193Notes

Reaction equation

HRID 2053193 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.[F: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]([F: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 2856454-Fluorophenylboronic acidHCID 178522031HCID 178522031, compound

Product 1

HCID 178522034HCID 178522034, compound

Procedure

The furyl bromide (84) (100 mg, 0.29 mmol) was coupled to 4-fluoro-phenylboronic acid (44 mg, 0.32 mmol) using Method E. The solvents were removed in vacuo as described, but the residue was dissolved in 2M NaOH (10 ml) and washed with EtOAc (2×10 ml). The aqueous layer was acidified to pH 1 with 2M HCl until a white precipitate formed and extracted with EtOAc (2×10 ml). The organic layer was dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound.

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionthe residue was dissolved in 2M NaOH (10 ml)
  3. washwashed with EtOAc (2×10 ml)
  4. customformed
  5. extractionextracted with EtOAc (2×10 ml)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-7c2feed64a334d5e8200b7c410a2b8e1
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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