HCID 22025700, compound → HCID 22025669, compound

HRID 1793023Notes

Reaction equation

HRID 1793023 reaction equation
[F:1][C:2]1[C:3]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]#[C:21][CH2:22][OH:23])=[CH:16][C:15]=2[F:24])=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5]([O:7][CH3:8])=[O:6]>CCO.[Pd]>[F:1][C:2]1[C:3]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][OH:23])=[CH:16][C:15]=2[F:24])=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 1

HCID 22025700HCID 22025700, compound

Product 1

HCID 22025669HCID 22025669, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 23938PalladiumSolvent

Procedure

Methyl 3,4-difluoro-2-[2-fluoro-4-(3-hydroxy-1-propynyl)anilino]benzoate was dissolved in absolute EtOH and hydrogenated in the presence of 5% Pd/C by the general procedure of Example 1, Step D. Purification of the resulting oil was carried out by column chromatography on silica gel (20% EtOAc/PE as eluant) to give methyl 3,4-difluoro-2-[2-fluoro-4-(3-hydroxypropyl)anilino]benzoate as a waxy white solid (93%), used directly in the next step. 1H NMR [400 MHz, (CD3)2SO] δ 8.81 (s, 1 H), 7.78 (ddd, J=9.0, 6.1, 2.0 Hz, 1 H), 7.10–7.02 (m, 2 H), 6.98 (ddd, J=8.3, 8.3, 4.0 Hz, 1 H), 6.94 (dd, J=8.2, 1.9 Hz, 1 H), 4.46 (t, J=4.8 Hz, 1 H), 3.82 (s, 3 H), 3.43–3.37 (m, 2 H), 2.58 (t, J=7.7 Hz, 2 H), 1.74–1.66 (m, 2 H). LCMS (APCI−) 338 (M−H).

Workup

  1. customPurification of the resulting oil

Sources & evidence

ORD record
ord-c2fd9b05bc69478ca881d4e35f1b42be
Source dataset
uspto-grants-2006_07
Patent number
US07078438B2

Reaction notes

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