HCID 89484871, compound → HCID 71547769, compound

HRID 1771149Notes

Reaction equation

HRID 1771149 reaction equation
C(=O)([O:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][CH:21]=[N:20]3)=[O:16])[C:9]=1[F:27])OC(C)(C)C>Cl.O1CCOCC1>[F:27][C:9]1[C:8]([OH:7])=[CH:13][CH:12]=[C:11]([F:14])[C:10]=1[C:15]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][CH:21]=[N:20]2)=[O:16]

Participants

3

Reactant 1

HCID 89484871HCID 89484871, compound

Product 1

HCID 71547769HCID 71547769, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A solution of tert-butyl (2,4-difluoro-3-(quinoxaline-6-carbonyl)phenyl) carbonate (1.06 g, 2.7 mmol, 1.0 eq.) in HCl/dioxane (2.5 N, 50 mL) was stirred at rt overnight, then concentrated. The residue was suspended in NaHCO3 solution, extracted with EA (10 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated. The residue was purified via flash column chromatography (PE/EA=2/1,v/v) to afford (2,6-difluoro-3-hydroxyphenyl) (quinoxalin-6-yl)methanone as a brown solid (600 mg, 77.7%). LRMS (M−H+) m/z calculated 285.1, found 285.0. 1H NMR (DMSO-d6, 400 MHz) δ 10.34 (s, 1 H), 9.09-9.12 (dd, 2 H), 8.39 (s, 1 H), 8.31-8.31 (d, 1 H), 7.14-7.27 (m, 2 H).

Workup

  1. concentrationconcentrated
  2. extractionextracted with EA (10 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified via flash column chromatography (PE/EA=2/1,v/v)

Sources & evidence

ORD record
ord-698ec61543764190ac9554e2d4be49ae
Source dataset
uspto-grants-2016_02
Patent number
US09249111B2

Reaction notes

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