HCID 46189870, compound → HCID 46205532, compound

HRID 1644755Notes

Reaction equation

HRID 1644755 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][C:13]([OH:15])=[O:14])[C:6]([CH3:16])=[C:5]2[C:17](=[O:28])[C:18]1[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][C:13]([OH:15])=[O:14])[C:6]([CH3:16])=[C:5]2[CH:17]([OH:28])[C:18]1[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:25])=[O:26])=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 46189870HCID 46189870, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 46205532HCID 46205532, compoundYield 18.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of [6-fluoro-4-(4-methanesulfonyl-benzoyl)-3-methyl-naphthalen-2-yl]-acetic acid (60 mg, 0.15 mmol) (example 6-1) in methanol (12 mL) was hydrogenated using a H-cube hydrogenation reactor with a flow rate of 1.7 mL/min and a 10% palladium on carbon catalyst cartridge at 20° C. under 10 bar hydrogen pressure. The reaction mixture was concentrated in vacuo. The crude product was purified using flash chromatography (RediSep® Flash column, 230-400 mesh, 2%-5% methanol in dichloromethane) to give 11 mg (18%) of {6-fluoro-4-[hydroxy-(4-methanesulfonyl-phenyl)-methyl]-3-methyl-naphthalen-2-yl}-acetic acid as an oil. 1H NMR (300 MHz, CDCl3) δ ppm: 7.82 (d, J=8.2 Hz, 2 H), 7.74 (dd, J=9.1, 6.0 Hz, 1 H), 7.61-7.70 (m, 2 H), 7.49 (d, J=8.2 Hz, 2 H), 7.15 (td, J=8.3, 2.1 Hz, 1 H), 6.73 (s, 1 H), 3.86 (br. s, 1 H), 3.48 (s, 2 H), 3.01 (s, 3 H), 2.41 (br. s, 3 H); HRMS (ESI+) cald. for C21H19FO5S [(M+Na)] 425.0829, obsd. 425.0827.

Workup

  1. customat 20° C.
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe crude product was purified

Sources & evidence

ORD record
ord-c709a0bfc3304c0e9a25b17ac6379cd2
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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