Methylamine → HCID 59451460, compound

HRID 1874845Notes

Reaction equation

HRID 1874845 reaction equation
Br[CH2:2][C:3]1[C:4]([F:20])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1.[CH3:21][NH2:22].C(OCC)(=O)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.C1COCC1>[Cl:19][C:17]1[CH:16]=[C:13]([CH:12]=[C:11]([O:10][C:5]2[C:6]([Cl:9])=[CH:7][CH:8]=[C:3]([CH2:2][NH:22][CH3:21])[C:4]=2[F:20])[CH:18]=1)[C:14]#[N:15]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 594515763-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile

Product 1

HCID 59451460HCID 59451460, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (1.04 g, 2.77 mmol) in CH2Cl2 (10 mL) was added dropwise to a 2M solution of MeNH2 (13.9 mL, 27.73 mmol) in THF. The solution turned light yellow and the flask was stoppered and stirred at RT overnight. Ethyl acetate (200 ml) and saturated NaHCO3 solution (150 ml) were added. The organic layer was separated, washed with brine (150 mL), dried over MgSO4, filtered and concentrated to give the title compound (0.81 g, 90%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.30-7.33 (m, 1H), 7.24-7.30 (m, 2H), 7.11-7.14 (m, 1H), 6.98 (dd, 1H), 3.81 (s, 2H), 2.45 (s, 3H).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine (150 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3b236e87029a4e1ba95f425d6ef5a760
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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