1,2-Dichloroethane → HCID 57575221, compound

HRID 533710Notes

Reaction equation

HRID 533710 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH:42]1[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([N:42]3[CH2:47][CH2:46][O:45][CH2:44][CH2:43]3)=[O:16])=[CH:17][CH:18]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 23533987HCID 23533987, compound

Product 1

HCID 57575221HCID 57575221, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-((3-fluorophenyl)ethynyl)benzoic acid (2.0 g, 8.33 mmol) and DIPEA (2.38 g, 18.3 mmol) in DMF (35 mL) was added EDC (1.86 g, 10.0 mmol), HOBt (1.35 g, 10.0 mmol) and morpholine (1.07 g, 12.5 mmol). The reaction was stirred at room temperature for 18 h. The reaction was diluted with water (200 mL) and extracted with EtOAc (2×150 mL). The combined organic extracts were washed with water (2×100 mL) and brine (100 mL), dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by column chromatography (silica gel) using 0 to 90% EtOAc/hexanes to afford (4-((3-fluorophenyl)ethynyl)phenyl)(morpholino)methanone (2.35 g, 89%) as a light tan solid; 1H-nmr (400 MHz, CDCl3) δ 7.57 (d, J=8.5 Hz, 2H), 7.41 (d, J=8.5 Hz, 2H), 7.38-7.31 (m, 2H), 7.28-7.21 (m, 1H), 7.13-7.05 (m, 1H), 4.00-3.31 (bd s, 8H); LC (290 nM) 5.08 min (>98%); MS (ESI) m/z=310.

Workup

  1. extractionextracted with EtOAc (2×150 mL)
  2. washThe combined organic extracts were washed with water (2×100 mL) and brine (100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-8450008550474ccab10273f2b17eba6c
Source dataset
uspto-grants-2014_10
Patent number
US08853392B2

Reaction notes

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