Tetramethylammonium fluoride → HCID 70978358, compound

HRID 1852110Notes

Reaction equation

HRID 1852110 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:12]([CH3:14])[CH3:13])=[CH:9][CH:10]=2)[C:5]([O:15][CH3:16])=[CH:4][N:3]=1.[F-:17].C[N+](C)(C)C>CS(C)=O.C(OC(=O)C)C>[F:17][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:12]([CH3:14])[CH3:13])=[CH:9][CH:10]=2)[C:5]([O:15][CH3:16])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 67803Tetramethylammonium fluorideHCID 86683193HCID 86683193, compound

Product 1

HCID 70978358HCID 70978358, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 1-chloro-4-methoxy-N,N-dimethylisoquinolin-6-amine (250 mg, 1.056 mmol) in DMSO (5 mL) was added tetramethylammonium fluoride (295 mg, 3.17 mmol) and the solution was heated to 110° C. for 1 h. The reaction was diluted with Ethylacteate and washed with water, and brine. The organic phase was collected, dried over sodium sulfate, and concentrated under vacuum to give the crude product which was purified by silica gel chromatography using 80% DCM/hexanes. The product fractions were collected and the solvent removed under vacuum to give 1-fluoro-4-methoxy-N,N-dimethylisoquinolin-6-amine (130 mg, 56% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.00 (d, J=9.3 Hz, 1H), 7.37 (d, J=1.3 Hz, 1H), 7.28-7.24 (m, 1H), 7.17 (s, 1H), 4.04 (s, 3H), 3.20 (s, 6H); MS m/z 221.0 (M++1).

Workup

  1. washwashed with water, and brine
  2. customThe organic phase was collected
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give the crude product which
  6. customwas purified by silica gel chromatography
  7. customThe product fractions were collected
  8. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-1ee41dc44f834de88f922f3cf8bda9ec
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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