Iodoethane → HCID 89618660, compound

HRID 2167745Notes

Reaction equation

HRID 2167745 reaction equation
I[CH2:2][CH3:3].[F:4][C:5]1[CH:6]=[CH:7][C:8]([OH:30])=[C:9]([C@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]2[CH:21]=[CH:20][N:19]3[N:22]=[CH:23][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:18]3[CH:17]=2)[CH:10]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.C(OCC)(=O)C>[CH2:28]([O:27][C:25]([C:24]1[CH:23]=[N:22][N:19]2[CH:20]=[CH:21][C:16]([N:12]3[CH2:13][CH2:14][CH2:15][C@@H:11]3[C:9]3[CH:10]=[C:5]([F:4])[CH:6]=[CH:7][C:8]=3[O:30][CH2:2][CH3:3])=[CH:17][C:18]=12)=[O:26])[CH3:29]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 89635862HCID 89635862, compound

Product 1

HCID 89618660HCID 89618660, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Iodoethane (0.17 g, 1.08 mmol) was added to a mixture of (R)-ethyl 5-(2-(5-fluoro-2-hydroxyphenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylate (Int-76) (0.2 g, 0.54 mmol) and K2CO3 (0.23 g, 1.62 mmol) in CH3CN (10 mL) and continued stirring at 80° C. for 16 h. The reaction mixture was diluted with ethyl acetate (100 mL), washed with water and dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude, which was purified by column chromatography (using silica gel and 2% ethyl acetate in hexane as eluent) to afford the desired compound (Int-77). MS (ESI): m/z 398.1 (M+H).

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude, which
  5. customwas purified by column chromatography (using silica gel and 2% ethyl acetate in hexane as eluent)

Sources & evidence

ORD record
ord-eaca5e38352c4fc0af67ad38415c9ca1
Source dataset
uspto-grants-2015_06
Patent number
US09045478B2

Reaction notes

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