Methyl morpholine oxide → HCID 58415363, compound

HRID 2075175Notes

Reaction equation

HRID 2075175 reaction equation
[CH2:1]([C:8]1[CH:16]=[CH:15][C:14]2[C:10](=[CH:11][N:12]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][C:18]=3[F:25])[N:13]=2)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>ClCCl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH2:1]([C:8]1[CH:16]=[CH:15][C:14]2[C:10](=[CH:11][N:12]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]=[O:24])=[CH:19][C:18]=3[F:25])[N:13]=2)[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 58415340HCID 58415340, compound

Product 1

HCID 58415363HCID 58415363, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of (4-(5-benzyl-2H-indazol-2-yl)-3-fluorophenyl)methanol (100 mg, 0.30 mmol), 4-methylmorpholine N-oxide (43 mg, 0.36 mmol) and activated molecular sieves (200 mg) in dichloromethane (10 mL) was added TPAP (10.6 mg, 0.03 mmol) at room temperature. After stirred overnight, the reaction mixture was filtered, concentrated and purified by silica gel column chromatography (hexane/ethyl acetate) to give 4-(5-benzyl-2H-indazol-2-yl)-3-fluorobenzaldehyde as white solid: 1H NMR (400 MHz, CD3OD) δ 10.0 (d, J=1.6 Hz, 1H), 8.55 (m, 1H), 8.41 (t, J=7.4 Hz, 1H), 7.84 (m, 2H), 7.68 (d, J=9.0 Hz, 1H), 7.46 (s, 1H), 7.34-7.30 (m, 2H), 7.27-7.19 (m, 4H), 4.06 (s, 2H); 19F NMR (376 MHz, CD3OD) δ −122.3. MS (ESI) m/z: Calculated: 330.36; Observed: 331.2 (M++1).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated
  3. custompurified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8677d03576c84ee582fcb1716872b7ba
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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