Iodoethane → HCID 73294553, compound

HRID 1398049Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=3[NH:15][CH2:16][CH3:17])[N:11]=[C:10]([CH:22]3[CH2:27][C:26]([CH3:29])([CH3:28])[O:25][C:24]([CH3:31])([CH3:30])[CH2:23]3)[CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:39][CH3:40]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=3[N:15]([CH2:39][CH3:40])[CH2:16][CH3:17])[N:11]=[C:10]([CH:22]3[CH2:27][C:26]([CH3:29])([CH3:28])[O:25][C:24]([CH3:30])([CH3:31])[CH2:23]3)[CH:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-[5-(4-chlorophenyl)-3-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)-1H-pyrazol-1-yl]-N-ethylaniline (Example 70) (25 mg, 0.06 mmol, 1 eq) in acetone (2 mL) was added potassium carbonate (84 mg, 0.6 mmol, 10 eq) and iodoethane (0.049 mL, 0.6 mmol, 10 eq), the solution heated to 60° C. overnight. The reaction was 50% complete, added iodoethane (0.049 mL) and heated to 60° C. overnight. Added water, extracted with DCM, dried over MgSO4 and concentrated. Purification by silica gel column chromatography (8 g) eluting with 7 to 15% EtOAc/hex, then purification by RP-HPLC eluting with 10 to 100% acetonitrile/H2O gave the title compound (12.4 mg, 46%).

Workup

temperatureheated to 60° C. overnight
extractionAdded water, extracted with DCM
dry with materialdried over MgSO4
concentrationconcentrated
customPurification by silica gel column chromatography (8 g)
washeluting with 7 to 15% EtOAc/hex
custompurification by RP-HPLC
washeluting with 10 to 100% acetonitrile/H2O

Sources & evidence

ORD record: ord-207b77e6e93f4efe91589dbeedf8a5fd
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901314B2

Reaction notes

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