Sulfuryl chloride → 6-(2-chloro-6-fluoro-3,5-dimethoxyphenyl)-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 1778764Notes

Reaction equation

HRID 1778764 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[CH:4][C:3]=1[C:12]1[N:17]=[CH:16][C:15]2[C:18]([I:27])=[N:19][N:20]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)[C:14]=2[CH:13]=1.S(Cl)([Cl:31])(=O)=O>C(Cl)Cl>[Cl:31][C:4]1[C:5]([O:10][CH3:11])=[CH:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[C:3]=1[C:12]1[N:17]=[CH:16][C:15]2[C:18]([I:27])=[N:19][N:20]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)[C:14]=2[CH:13]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 867228616-(2-fluoro-3,5-dimethoxyphenyl)-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 867228606-(2-chloro-6-fluoro-3,5-dimethoxyphenyl)-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridineYield 67.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At r.t. to a solution of 6-(2-fluoro-3,5-dimethoxyphenyl)-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine (35 mg, 0.072 mmol) (Example 52, Step 4) in methylene chloride (3 mL) was added sulfuryl chloride (7.0 μL, 0.087 mmol). The mixture was stirred at r.t. for 20 min then concentrated. The solid was filtered out and the crude material was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.025 g). LCMS (M+H)+=518.1.

Workup

  1. concentrationthen concentrated
  2. filtrationThe solid was filtered out
  3. customthe crude material was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record
ord-f6cfcd7af21749d898f58e1e3575add9
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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