3-Chloro-4-fluoroaniline → HCID 57580568, compound

HRID 2261031Notes

Reaction equation

HRID 2261031 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][O:15][CH2:16][C:17]2[CH:18]=[CH:19][N:20]3[C:25]=2[C:24](SC)=[N:23][CH:22]=[N:21]3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[Cl:39][C:40]1[CH:41]=[C:42]([CH:44]=[CH:45][C:46]=1[F:47])[NH2:43]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][O:15][CH2:16][C:17]2[CH:18]=[CH:19][N:20]3[C:25]=2[C:24]([NH:43][C:42]2[CH:44]=[CH:45][C:46]([F:47])=[C:40]([Cl:39])[CH:41]=2)=[N:23][CH:22]=[N:21]3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 97083-Chloro-4-fluoroanilineHCID 70297m-Chloroperbenzoic acidHCID 57580579HCID 57580579, compound

Product 1

HCID 57580568HCID 57580568, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 2-(4-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethoxymethyl)-morpholine-4-carboxylic acid tert-butyl ester (60 mg, 0.15 mmol) in CH2Cl2 (3 mL) was cooled to 0 C and treated with a solution of mCPBA (56 mg, 0.32 mmol) in CH2Cl2 (2 mL). The reaction was stirred for 15 minutes at 0 C then warmed to room temperature. To this solution was added 3-chloro-4-fluoroaniline and stirred at room temperature for one hour. The resulting orange solution was diluted with CH2Cl2 and washed with saturated aqueous NaHCO3, then saturated aqueous NaCl. The organic layer was dried (Na2SO4), filtered and concentrated. Preparative reverse-phase HPLC afforded the desired compound (30 mg, 41%). HPLC tR=4.383 min (YMC S5 ODS 4.6×50 mm, 10-90% aqueous methanol, 4 min gradient, monitored at 220 nm). LC/MS (M+H)=492.

Workup

  1. stirringstirred at room temperature for one hour
  2. washwashed with saturated aqueous NaHCO3
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-209f68cec6784b3f8ae1b8731b4a4326
Source dataset
uspto-grants-2010_12
Patent number
US07846931B2

Reaction notes

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