Selectfluor → 4-amino-8-(cyclopentyloxy)-3-fluoro-7-methoxy-2H-chromen-2-one

HRID 20642

Reaction equation

HRID 20642 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([O:14][CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[O:5][C:4](=[O:20])[CH:3]=1.[B-](F)(F)(F)[F:22].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([O:14][CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[O:5][C:4](=[O:20])[C:3]=1[F:22]

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 771747934-amino-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

Product 1

HCID 866181344-amino-8-(cyclopentyloxy)-3-fluoro-7-methoxy-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-amino-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (100 mg, 0.36 mmol, Example 3, Step 1), Selectfluor (160 mg, 0.45 mmol), and acetonitrile (1.5 mL) were stirred vigorously for 18 h, concentrated, and then purified by silica gel chromatography (7:3→1:4; hexanes:ethyl acetate) to give 4-amino-8-(cyclopentyloxy)-3-fluoro-7-methoxy-2H-chromen-2-one: MS (ESI): 294.0.

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel chromatography (7:3→1:4; hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-1f2b2ae8e5f1496aafb24688b567536b
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Linked notes

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