Thionyl Chloride → 4-(4-(Chloromethyl)-2-(1-vinylcyclopentyl)phenyl)-5-fluoro-2-methoxypyridine

HRID 404392Notes

Reaction equation

HRID 404392 reaction equation
[F:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16]O)=[CH:12][C:11]=2[C:18]2([CH:23]=[CH2:24])[CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.S(Cl)([Cl:27])=O>CN(C=O)C.C(Cl)Cl>[Cl:27][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([C:3]2[C:2]([F:1])=[CH:7][N:6]=[C:5]([O:8][CH3:9])[CH:4]=2)=[C:11]([C:18]2([CH:23]=[CH2:24])[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:12]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 57706064(4-(5-Fluoro-2-methoxypyridin-4-yl)-3-(1-vinylcyclopentyl)phenyl)methanol

Product 1

HCID 574676564-(4-(Chloromethyl)-2-(1-vinylcyclopentyl)phenyl)-5-fluoro-2-methoxypyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-(5-fluoro-2-methoxypyridin-4-yl)-3-(1-vinylcyclopentyl)phenyl)methanol (47.0 mg, 144 μmol) in DMF (0.01 mL) and DCM (4.0 mL) was slowly added thionyl chloride (14.7 μL, 201 μmol) at 0° C. After addition, the resulting mixture was stirred at room temperature for 1 hour. The solvent was removed, and the product thus obtained was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 8.01-8.11 (1H, m), 7.98 (1H, m), 7.47 (1H, s), 6.94 (1H, d, J=7.8 Hz), 6.69-6.82 (1H, m), 5.80 (1H, dd, J=17.2, 10.6 Hz), 4.89 (1H, d, J=10.2 Hz), 4.52-4.69 (3H, m), 3.89 (3H, s), 1.68-1.84 (4H, m), 1.49-1.67 (4H, m).

Workup

  1. customat 0° C
  2. additionAfter addition
  3. customThe solvent was removed
  4. customthe product thus obtained
  5. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-6ebe1200df6541508a6e88bee26d8b77
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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