Triethylamine → HCID 66616643, compound

HRID 1889671Notes

Reaction equation

HRID 1889671 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14].[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH2:23])=[CH:18][CH:17]=1.C(N(CC)CC)C>C1COCC1>[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH:23][CH2:2][C:3]2[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=2[O:13][CH3:14])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoate

Product 1

HCID 66616643HCID 66616643, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(bromomethyl)-3-methoxybenzoate (0.518 g, 2 mmol, Trans World Chemicals) in THF (10 mL) at room temperature was added (4-fluorophenyl)methanamine (1.00 g, 8.00 mmol, Aldrich) and triethylamine (0.56 mL, 4 mmol). The reaction mixture was stirred at rt for 1 h and quenched by the addition of 5 mL of saturated aq. NaHCO3 solution. The resulting mixture was extracted with DCM (3×50 mL). The combined organic extracts were dried over MgSO4 and concentrated. The residue was purified by flash column chromatography (ISCO system, eluting with CH2Cl2/EtOAc) to give the desired compound (0.35 g, 57%) as a white solid. 1H NMR (CD3OD) δ 7.64 (d, 1H, J=6.0 Hz), 7.60 (s, 1H), 7.40 (d, 2H, J=7.7 Hz), 7.36 (d, 1H, J=6.0 Hz), 7.08 (t, 211, J=7.7 Hz), 3.97 (s, 3H), 3.96 (s, 3H), 3.82 (s, 2H), 3.76 (s, 2H). MS (ESI): 304.1 (M+H)+.

Workup

  1. customquenched by the addition of 5 mL of saturated aq. NaHCO3 solution
  2. extractionThe resulting mixture was extracted with DCM (3×50 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (ISCO system, eluting with CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-04c5c58c70c6413eae16db87f6e0f245
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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