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Tetrahydrofuran → HCID 86651052, compound

HRID 884880
Notes
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Reaction equation

HRID 884880 reaction equation
[Cl:1][C:2]1[CH:27]=[N:26][CH:25]=[CH:24][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([C:13]([F:22])([C:18]([F:21])([F:20])[F:19])[C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9][C:8]=1O)=[O:5].O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:27]=[N:26][CH:25]=[CH:24][C:3]=1[C:4]1[O:5][C:8]2[CH:9]=[CH:10][C:11]([C:13]([F:22])([C:18]([F:20])([F:19])[F:21])[C:14]([F:17])([F:16])[F:15])=[CH:12][C:7]=2[N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86651053HCID 86651053, compound

Product 1

HCID 86651052HCID 86651052, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

To a mixture of 0.90 g of 3-chloro-N-[2-hydroxy-5-(heptafluoroisopropyl)phenyl]isonicotinamide, 10 ml of tetrahydrofuran and 0.68 g of triphenylphosphine, 1.13 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature. The reaction mixture was stirred for 1.2 hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.58 g of 2-(3-chloropyridin-4-yl)-5-(heptafluoroisopropyl)benzoxazole (hereinafter, referred to as “active compound 68”).

Workup

  1. additionwas added dropwise at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a3bfc7821944440cac3a1ed00d899de2
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08242133B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes