2-[4-(2,4-Difluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 69020799, compound

HRID 1865096Notes

Reaction equation

HRID 1865096 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[C:8]([CH2:14][CH3:15])=[C:9]([C:12]#[N:13])[C:10]=1I)=[O:5])[CH3:2].[F:17][C:18]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:19]=1[O:20][C:21]1[CH:26]=[CH:25][C:24](B2OC(C)(C)C(C)(C)O2)=[CH:23][CH:22]=1>>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[C:8]([CH2:14][CH3:15])=[C:9]([C:12]#[N:13])[C:10]=1[C:24]1[CH:23]=[CH:22][C:21]([O:20][C:19]2[CH:36]=[CH:37][C:38]([F:40])=[CH:39][C:18]=2[F:17])=[CH:26][CH:25]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 579752142-[4-(2,4-Difluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 57975348HCID 57975348, compound

Product 1

HCID 69020799HCID 69020799, compound

Procedure

Prepare the title compound in the manner analogous to the procedure set fourth in the final step of example E-227 using 4-cyano-5-ethyl-3-iodo-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (prepared in preparation 38) and 2-[4-(2,4-difluoro-phenoxy)-phenyl]-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane. Purify the material by silica gel chromatography (Chromatotron™) eluting with hexane/ethyl acetate 4:1 to provide the final title compound, 4-cyano-5-ethyl-3-[4-(2,4-difluoro-phenoxy)-phenyl]-1-methyl-1H-pyrole-2-carboxylic acid ethyl ester, as a tan solid. Mass spectrum (m/e): 411.1 (M*+1): (Bruker 300) 1H NMR (CDCl3) δ 7.27-7.31 (2H, d), 7.07-7.14 (1H, m), 6.74-6.97 (4H, m), 4.04-4.11 (2H, dd), 3.84-3.88 (3H, s), 2.78-2.89 (2H, dd), 1.23-1.34 (3H, t), 1.00-1.06 (3H, t).

Workup

  1. customPurify the material by silica gel chromatography (Chromatotron™)
  2. washeluting with hexane/ethyl acetate 4:1

Sources & evidence

ORD record
ord-ba82ba92adca4844a2b14e00405ccacd
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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