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

HRID 1641294
Notes
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Reaction equation

HRID 1641294 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 Tetroxide
Catalyst
HCID 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) (1000 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-bc2d41c8957e4d47acf9a301971394ab
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08114873B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes