tert-Butanol → HCID 67486075, compound

HRID 1809588Notes

Reaction equation

[Br:1][C:2]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[C:6](C(O)=O)=[N:7][CH:8]=[C:9]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[CH:10]=1.[CH3:28][C:29]([OH:32])([CH3:31])[CH3:30].C([N:35]([CH2:38]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:47])=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[C:6]([NH:35][C:38](=[O:47])[O:32][C:29]([CH3:31])([CH3:30])[CH3:28])=[N:7][CH:8]=[C:9]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A 500 mL flask was charged with 3-(2-bromo-4-fluorophenoxy)-5-(3-methoxyphenylthio)picolinic acid (10.0 g, 22.2 mmol), 2-methylpropan-2-ol (11.6 mL, 133 mmol), triethylamine (4.0 mL, 28.9 mmol), and Toluene (200 mL). The reaction was heated to 100° C. and DPPA (4.8 mL, 22.2 mmol) was added dropwise. The reaction was stirred for 10 minutes, then cooled to ambient temperature, poured into dilute NaOH and extracted with EtOAc. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica (10 to 20% EtOAc in hexanes) to afford tert-butyl 3-(2-bromo-4-fluorophenoxy)-5-(3-methoxyphenylthio)pyridin-2-ylcarbamate (8.4 g, 72.5% yield).

Workup

temperaturecooled to ambient temperature
extractionextracted with EtOAc
dry with materialThe organic layer was dried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified on silica (10 to 20% EtOAc in hexanes)

Sources & evidence

ORD record: ord-9d080e29fab54b5096ab0cc579a5ba4f
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362037B2

Reaction notes

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