Sodium Carbonate → Morpholin-4-yl(5-nitrobiphenyl-3-yl)methanone

HRID 530386Notes

Reaction equation

HRID 530386 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[O:12])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>COCCOC.O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:13]1([C:11]([C:4]2[CH:3]=[C:2]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=2)=[O:12])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 80271Tri-o-tolylphosphineHCID 26369864(3-Bromo-5-nitrophenyl)(morpholino)methanone

Product 1

HCID 90041337Morpholin-4-yl(5-nitrobiphenyl-3-yl)methanone

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of (3-bromo-5-nitrophenyl)(morpholin-4-yl)methanone (200 mg, 0.635 mmol), phenylboronic acid (101 mg, 0.825 mmol), sodium carbonate (101 mg, 0.952 mmol), tri-o-tolylphosphine (19.32 mg, 0.063 mmol) and palladium(II) acetate in DME (1.02 mL) and water (0.25 mL) was heated to 100° C. for 3 hours, then allowed to cool to room temperature. The mixture was diluted with ethyl acetate (50 mL), filtered through CELITE, and washed with brine (30 mL). The organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate:hexanes) provided morpholin-4-yl(5-nitrobiphenyl-3-yl)methanone as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3) δ 8.53 (t, J=1.6 Hz, 1H), 8.25 (s, 1H), 7.98 (s, 1H), 7.65 (d, J=7.3 Hz, 2H), 7.61-7.43 (m, 3H), 3.69 (dd, J=65.5, 62.1 Hz, 8H).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered through CELITE
  3. washwashed with brine (30 mL)
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-7fae5584131e4385a2da09839b291b32
Source dataset
uspto-grants-2016_05
Patent number
US09353066B2

Reaction notes

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