Methanesulfonyl chloride → HCID 57425777, compound

HRID 1360128Notes

Reaction equation

HRID 1360128 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:22])[CH:9]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C1COCC1.C([O-])(O)=O.[Na+]>[CH3:32][S:33]([O:22][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:9]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)(=[O:35])=[O:34]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 57425775HCID 57425775, compound

Product 1

HCID 57425777HCID 57425777, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To the solution of 1-(4-fluorophenyl)-2,2-dipyridin-3-ylethanol (0.2 g, 0.68 mmol) in THF (4 mL) was added i-Pr2NEt (0.4 mL, 2.3 mmol) at 0° C. followed by methanesulfonyl chloride (0.1 mL, 1.3 mmol). The reaction mixture was stirred for 10 h. Diluted with saturated NaHCO3 and extracted with CH2Cl2. The combined organic layer was dried, filtered, and concentrated to give 1-(4-fluorophenyl)-2,2-dipyridin-3-ylethyl methanesulfonate. LRMS m/z (M+H) Calcd: 373.4. found: 373.0.

Workup

  1. extractionextracted with CH2Cl2
  2. customThe combined organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b45371c9c54c466aa8b94c9e5b2dd0bf
Source dataset
uspto-grants-2011_02
Patent number
US07879839B2

Reaction notes

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