Water → HCID 58368604, compound
Reaction equation
[Cl-].[NH4+].O.[Cl:4][C:5]1[CH:6]=[C:7]([C:27]([O:29][CH3:30])=[O:28])[C:8]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[C:9]([N+:17]([O-])=O)[C:10]=1[C:11]#[C:12][Si:13]([CH3:16])([CH3:15])[CH3:14]>>[NH2:17][C:9]1[C:10]([C:11]#[C:12][Si:13]([CH3:15])([CH3:14])[CH3:16])=[C:5]([Cl:4])[CH:6]=[C:7]([C:27]([O:29][CH3:30])=[O:28])[C:8]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1Participants
Conditions
- Temperature
- 60 °C
Procedure
The reaction mixture was treated with 5 M ammonium chloride in water (4.1 mL, 21 mmol) followed by methyl 4-chloro-3′-fluoro-6-nitro-5-[(trimethylsilyl)ethynyl]biphenyl-2-carboxylate (1.9 g, 4.8 mmol) and heated at 60° C. for 16 hours. The reaction mixture was filtered over celite, washed with methanol, and the filtrate was concentrated to a solid. The solid was diluted with ethyl acetate (200 mL) and saturated sodium bicarbonate (100 mL) and stirred for a few minutes. The organic layer was separated, washed with brine, dried with sodium sulfate, filtered, and concentrated to a crude residue. Purification by flash column chromatography using ethyl acetate in hexanes (0%-10%) gave the desired product (1.5 g, 86%). LCMS for C19H20ClFNO2Si (M+H)+: m/z=376.1; Found: 376.1.
Workup
- filtrationThe reaction mixture was filtered over celite
- washwashed with methanol
- concentrationthe filtrate was concentrated to a solid
- additionThe solid was diluted with ethyl acetate (200 mL) and saturated sodium bicarbonate (100 mL)
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated to a crude residue
- customPurification by flash column chromatography
Sources & evidence
- ORD record
- ord-1cf403b5c44e4a8f8a4a702f71d0bb09
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108984B2
Reaction notes
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