Water → HCID 58474850, compound

HRID 1400862Notes

Reaction equation

HRID 1400862 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.CC(C)([O-])C.[Na+].Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]2[CH:23]=[C:24]([C:26]3[N:31]=[CH:30][C:29]([CH2:32][N:33]4[CH2:38][CH2:37][CH2:36][O:35][C:34]4=[O:39])=[CH:28][CH:27]=3)[S:25][C:18]=12.O>CS(C)=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:17]2[CH:22]=[CH:21][N:20]=[C:19]3[CH:23]=[C:24]([C:26]4[N:31]=[CH:30][C:29]([CH2:32][N:33]5[CH2:38][CH2:37][CH2:36][O:35][C:34]5=[O:39])=[CH:28][CH:27]=4)[S:25][C:18]=23)=[C:4]([F:9])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2735918Phenol, 4-amino-2-fluoro-HCID 23676156Sodium t-butoxideHCID 58474635HCID 58474635, compound

Product 1

HCID 58474850HCID 58474850, compoundYield 117.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-amino-2-fluorophenol (70.7 mg, 0.556 mmol) in DMSO (5 mL) was added sodium tert-butoxide (53.4 mg, 0.556 mmol) and the reaction mixture was stirred for 30 min. Chloride 199 (100 mg, 0.278 mmol) was added and the reaction mixture was heated at 100° C. overnight. The mixture was then cooled to RT and poured into water (20 mL) and the precipitated product was collected by filtration and purified by Biotage (MeOH/EtOAc 0-50%, SNAP 25 g cartridge) to give title compound 200 (147 mg, 33% yield) as a beige solid. MS: 451 (MH+).

Workup

  1. temperatureThe mixture was then cooled to RT
  2. filtrationthe precipitated product was collected by filtration
  3. custompurified by Biotage (MeOH/EtOAc 0-50%, SNAP 25 g cartridge)

Sources & evidence

ORD record
ord-110a8846e189427083d893e6b29d55f6
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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