HCID 68295707, compound → HCID 68295789, compound

HRID 572497Notes

Reaction equation

HRID 572497 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:13]([C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]([OH:19])=[O:18])=O)[C:5]([CH3:12])=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][CH2:7]2.[H][H]>C(O)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH2:13][C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]([OH:19])=[O:18])[C:5]([CH3:12])=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 68295707HCID 68295707, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68295789HCID 68295789, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-(8-fluoro-5-methylchroman-6-carbonyl)benzoic acid (673 mg, 2.141 mmol) in acetic Acid (15 mL) was treated with Pd/C (60.0 mg) and the mixture was stirred under 50 psi of hydrogen at 65° C. until the reaction was judged complete by LCMS. The mixture was filtered over Celite and the filtrate was concentrated to give the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.80-2.05 (m, 5 H), 2.63 (t, J=6.44 Hz, 2 H), 3.95-4.15 (m, 2 H), 4.24 (s, 2 H), 6.57 (d, J=12.29 Hz, 1 H), 6.95 (d, J=7.61 Hz, 1 H), 7.21-7.34 (m, 1 H), 7.42 (td, J=7.56, 1.27 Hz, 1 H), 7.81 (dd, J=7.71, 1.07 Hz, 1 H), 12.92 (br. s., 1H); LC/MS (m/z) ES+=301 (M+1).

Workup

  1. filtrationThe mixture was filtered over Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-774bfb58e456471cbe2fe5a3ccfa742e
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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