Iodoethane → HCID 89618660, compound

HRID 1476778Notes

Reaction equation

HRID 1476778 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-f1a778a3ce8f41dea33b1d6da93ce782
Source dataset
uspto-grants-2016_08
Patent number
US09402833B2

Reaction notes

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