p-Toluenesulfonic acid → HCID 131733005, compound

HRID 2177597Notes

Reaction equation

HRID 2177597 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][C:17]2[C:20]([I:23])=[N:21][NH:22][C:16]=2[CH2:15]1)=[O:13].[O:24]1[CH:29]=[CH:28][CH2:27][CH2:26][CH2:25]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC(Cl)C.C(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:9])[F:10])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][C:17]2[C:20]([I:23])=[N:21][N:22]([CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29][O:24]3)[C:16]=2[CH2:15]1)=[O:13].[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:9])[F:10])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][C:17]2[CH:20]([I:23])[N:21]([CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29][O:24]3)[NH:22][C:16]=2[CH2:15]1)=[O:13]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 90409002HCID 90409002, compound

Product 1

HCID 131733005HCID 131733005, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 6-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-iodo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine (40 mg, 0.09 mmol) in dichloroethane (1 mL) was added 3,4-dihydropyran (24 mL, 0.26 mmol) and para-toluenesulfonic acid (2 mg, 0.009 mmol). After stirring for 4 h at rt the reaction was diluted with CH2Cl2 and washed with aqueous saturated sodium bicarbonate. The organic layer was dried over anhydrous MgSO4, filtered and concentrated. Chromatography on silica gel (0-50% ethyl acetatehexanes) provided the desired product as a mixture of regioisomers (45 mg, 95%). MS (ESI) mass calcd. C19H18ClF31N3O2, 539.0. m/z found, 540.0 [M+H]+.

Workup

  1. washwashed with aqueous saturated sodium bicarbonate
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8ba80095e77d438aba69193774d01fec
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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