Propargyl alcohol → HCID 22025700, compound

HRID 1793022Notes

Reaction equation

HRID 1793022 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[F:5][C:6]1[C:7]([NH:17][C:18]2[CH:23]=[CH:22][C:21](I)=[CH:20][C:19]=2[F:25])=[C:8]([CH:13]=[CH:14][C:15]=1[F:16])[C:9]([O:11][CH3:12])=[O:10]>>[F:5][C:6]1[C:7]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:3]#[C:2][CH2:1][OH:4])=[CH:20][C:19]=2[F:25])=[C:8]([CH:13]=[CH:14][C:15]=1[F:16])[C:9]([O:11][CH3:12])=[O:10]

Participants

3

Reactant 2

HCID 7859Propargyl alcoholHCID 22025654HCID 22025654, compound

Product 1

HCID 22025700HCID 22025700, compoundYield 94%

Procedure

The title compound was prepared by Sonogashira reaction of propargyl alcohol and methyl 3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoate by the general procedure of Example 1, Step A. The oil resulting from workup was purified by chromatography on silica gel (20% EtOAc/PE as eluant), to give methyl 3,4-difluoro-2-[2-fluoro-4-(3-hydroxy-1-propynyl)anilino]benzoate as a pale yellow solid (94%); m.p. (Et2O/hexane) 116–120° C. 1H NMR [400 MHz, (CD3)2SO] δ 8.79 (s, 1H), 7.79 (ddd, J=8.3, 5.9, 2.0 Hz, 1 H), 7.30 (dd, J=12.2, 1.8 Hz, 1 H), 7.26–7.17 (m, 1 H), 7.15 (dd, J=8.5, 1.6 Hz, 1 H), 6.92 (ddd, J=8.8, 8.8, 4.7 Hz, 1 H), 5.31 (br s, 1 H), 4.28 (s, 2 H), 3.81 (s, 3 H). Anal. calcd. for C17H12F3NO3: C, 60.9; H, 3.6; N, 4.2. Found C, 61.4; H, 3.9; N, 4.7.

Workup

  1. customThe oil resulting from workup
  2. customwas purified by chromatography on silica gel (20% EtOAc/PE as eluant)

Sources & evidence

ORD record
ord-3d3cfd5131e3410bbcdb5fd0eff6d6d5
Source dataset
uspto-grants-2006_07
Patent number
US07078438B2

Reaction notes

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