Diethyl Ether → HCID 90047122, compound

HRID 1505004Notes

Reaction equation

HRID 1505004 reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][C:13]=1[F:19].[C:20](#N)C.CCOCC>C(OC)(OC)OC>[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][CH:20]=[C:5]2[C:6](=[O:8])[O:7][C:2]([CH3:10])([CH3:1])[O:3][C:4]2=[O:9])=[CH:14][C:13]=1[F:19]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6342AcetonitrileHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 8218484-Bromo-3-fluoroaniline

Product 1

HCID 90047122HCID 90047122, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,2-dimethyl-1,3-dioxane-4,6-dione (36.4 g, 253 mmol) in trimethyl orthoformate (125 mL) was stirred at 100° C. for 1.5 h. This mixture was cooled to 80° C. and 4-bromo-3-fluoroaniline (40 g, 211 mmol) was added using ACN to aid in transfer. Heated to 100° C. for 3.5 h. The reaction mixture was cooled to RT and poured into Et2O (750 mL) and stirred for a few minutes. Filtered resulting solid, washing with Et2O and dried to yield 5-(((4-bromo-3-fluorophenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (61.41 g, 178 mmol, 85% yield) as a light yellow powder. 1H NMR (DMSO-d6) δ ppm 11.25 (d, J=14.4 Hz, 1H), 8.59 (d, J=14.4 Hz, 1H), 7.67-7.85 (m, 2H), 7.42 (dd, J=8.6, 2.0 Hz, 1H), 1.68 (s, 6H).

Workup

  1. temperatureThis mixture was cooled to 80° C.
  2. temperatureHeated to 100° C. for 3.5 h
  3. temperatureThe reaction mixture was cooled to RT
  4. stirringstirred for a few minutes
  5. filtrationFiltered
  6. customresulting solid
  7. washwashing with Et2O
  8. customdried

Sources & evidence

ORD record
ord-300cdfd527364971b2f8cb948e56ea88
Source dataset
uspto-grants-2015_12
Patent number
US09216965B2

Reaction notes

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