Water → 3-fluoro-N-(4-formyl-naphthalen-1-yl)-5-morpholin-4-yl-benzamide

HRID 1171426Notes

Reaction equation

HRID 1171426 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH:26]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]=CCCCC)=[CH:10][CH:9]=1)=[O:6].O.I([O-])(=O)(=O)=[O:35].[Na+]>C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([N:27]2[CH2:28][CH2:29][O:30][CH2:31][CH2:32]2)[CH:26]=1)[C:5]([NH:7][C:8]1[C:13]2[C:12](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:11]([CH:18]=[O:35])=[CH:10][CH:9]=1)=[O:6]

Participants

6

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 667379733-fluoro-N-(4-hex-1-enyl-naphthalen-1-yl)-5-morpholin-4-yl-benzamide

Product 1

HCID 595531113-fluoro-N-(4-formyl-naphthalen-1-yl)-5-morpholin-4-yl-benzamideYield 45.3%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred room temperature solution of 3-fluoro-N-(4-hex-1-enyl-naphthalen-1-yl)-5-morpholin-4-yl-benzamide (2.7 g, 6.25 mmol) THF (15 ml) and water (5 ml) is added osmium tetroxide (2.5% in t-butanol) (100 μl) and sodium periodate (6 g) in portions over 30 minutes. After 1.5 hours, the mixture is diluted with ethyl acetate (200 ml) and washed with water (2×100 ml). The organic layer is dried over anhydrous sodium sulfate and evaporated to dryness. The residue is purified by column chromatography on silica gel eluting with 25-30% ethyl acetate in hexanes to give 3-fluoro-N-(4-formyl-naphthalen-1-yl)-5-morpholin-4-yl-benzamide as a tan powder (1.072 g). Mp: 204-5° C. 1H NMR 400 MHz (CDCl3) δ 10.3 (s, 1H), 9.41 (d, 1H, J=8.8 Hz), 8.47 (d, 2H, J=7.6 Hz), 8.02 (d, 1H, J=8 Hz), 7.92 (d, 1H, J=8.4 Hz), 7.65-7.76 (m, 2H), 7.31 (s, 1H), 7.05 (d, 1H, J=8 Hz), 6.79 (d, 1H, J=11.6 Hz), 3.88 (t, 4H, J=5.2 Hz), 3.27 (t, 4H, J=5.2 Hz). MS: 379 (M+1).

Workup

  1. washwashed with water (2×100 ml)
  2. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe residue is purified by column chromatography on silica gel eluting with 25-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ecb7cf1178414bd9bb2f3612145135e9
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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