Nitrilooxonium tetrafluoroborate → HCID 87503465, compound

HRID 638994Notes

Reaction equation

HRID 638994 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[C:7]([F:14])[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[NH2:15].[F:16][B-:17]([F:20])([F:19])[F:18].[N:21]#[O+]>C1COCC1>[F:16][B-:17]([F:20])([F:19])[F:18].[Br:1][C:2]1[C:11]2[C:6](=[C:7]([F:14])[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:15]#[N:21]

Participants

4

Reactant 2

HCID 11137142Nitrilooxonium tetrafluoroborateHCID 68576477HCID 68576477, compound

Product 1

HCID 87503465HCID 87503465, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-2 °C

Procedure

A solution of 4-bromo-8-fluoro-6-(methoxy)-3-quinolinamine (3 g, 11.1 mmol) in anhydrous THF (40 mL) cooled down to −9° C., with an ethanol/ice bath, was treated with nitrosonium tetrafluoroborate (1.4 g, 12.2 mmol) added portionwise over 20 minutes. The reaction mixture was stirred for 30 minutes at −2° C. under argon atmosphere. A precipitate was formed which was filtered, washed with cold THF and dried in vacuo overnight to afford the product as a yellow solid (3.2 g, 79%). MS (+ve ion electrospray) m/z 370 (MH+).

Workup

  1. additionadded portionwise over 20 minutes
  2. customA precipitate was formed which
  3. filtrationwas filtered
  4. washwashed with cold THF
  5. customdried in vacuo overnight

Sources & evidence

ORD record
ord-69d1cf2b71374fc3b2e1fe5810a0253c
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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