Isopropanol → US9249085, II(d)

HRID 1771771Notes

Reaction equation

HRID 1771771 reaction equation
[F:1][C:2]1[C:12]([NH:13][CH2:14][C:15]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=3)[CH:18]=[CH:17][C:16]=2[F:28])=[C:11]([F:29])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7].[CH3:30][CH:31](O)[CH3:32]>S(=O)(=O)(O)O>[F:1][C:2]1[C:12]([NH:13][CH2:14][C:15]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=3)[CH:18]=[CH:17][C:16]=2[F:28])=[C:11]([F:29])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([O:8][CH:31]([CH3:32])[CH3:30])=[O:7]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 715155142-[2,4-Difluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetic acid

Product 1

HCID 71503443US9249085, II(d)Yield 68%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

2-[2,4-Difluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetic acid (I(b)) (70 mg, 0.17 mmol, 1.0 eq) was dissolved in iPrOH (5 mL). Concentrated sulphuric acid (2 drops) was added and the solution was stirred at room temperature overnight. The reaction was quenched by addition of aqueous NaHCO3 and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo to give the crude product. The compound was triturated in a mixture of petroleum ether and DCM and dried under vacuum to give the title compound (II(d)) as a gummy solid (52 mg, 68%).

Workup

  1. customThe reaction was quenched by addition of aqueous NaHCO3
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give the crude product
  7. customThe compound was triturated in a mixture of petroleum ether and DCM
  8. customdried under vacuum

Sources & evidence

ORD record
ord-86f4a39cd4cc4176ad74e17a24e0cd7f
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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