Thionyl Chloride → HCID 86685947, compound

HRID 2277629Notes

Reaction equation

HRID 2277629 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:21])([CH3:20])[N:7]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH2:18]O)[CH:17]=3)[C:8]2=[O:11])=[CH:4][CH:3]=1.S(Cl)([Cl:24])=O>C(Cl)Cl>[Cl:24][CH2:18][C:16]1[CH:17]=[C:12]([N:7]2[C:6]([CH3:21])([CH3:20])[C:5]3[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)[C:8]2=[O:11])[CH:13]=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 866859461H-Isoindol-1-one, 6-fluoro-2,3-dihydro-2-[5-(hydroxymethyl)-3-pyridinyl]-3,3-dimethyl-

Product 1

HCID 86685947HCID 86685947, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
3.5 °C

Procedure

To a solution of 6-fluoro-2-(5-hyroxymethyl-pyridin-3-yl)-3,3-dimethyl-2,3-dihydro-isoindol-1-one (52 mg) in DCM (10 mL) was added thionyl chloride (0.14 mL, 1.9 mmol) slowly at 0° C. After the addition, the reaction mixture was stirred at 2-5° C. for 0.5 hour before it was poured into satd. aq. NaHCO3 solution (10 mL) and extracted with DCM (2×15 mL). The combined organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product (58 mg 100%) as light yellowish solid. MS: 322.1 (M+H+).

Workup

  1. additionAfter the addition
  2. additionwas poured into satd
  3. extractionaq. NaHCO3 solution (10 mL) and extracted with DCM (2×15 mL)
  4. washThe combined organic layers were washed with brine
  5. customdried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fba1f4f0999e45b28c2c443e74021c32
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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