Methanesulfonyl chloride → (2-Chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-6-yl)methyl methanesulfonate

HRID 595717Notes

Reaction equation

HRID 595717 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH:7]([CH2:12][OH:13])[N:6]3[C:14]4[CH:15]=[CH:16][CH:17]=[C:18]([F:21])[C:19]=4[CH:20]=[C:5]3[C:4]=2[N:3]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C1COCC1>[CH3:22][S:23]([O:13][CH2:12][CH:7]1[N:6]2[C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([F:21])[C:19]=3[CH:20]=[C:5]2[C:4]2[N:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:9]=2[CH2:8]1)(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 90333617(2-Chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-6-yl)methanol

Product 1

HCID 90333629(2-Chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-6-yl)methyl methanesulfonateYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (2-chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-6-yl)methanol (200 mg, 0.66 mmol) and TEA (200 mg, 1.98 mmol) in THF (8 mL) was stirred at 0° C. and MsCl (114 mg, 0.99 mmol) was added dropwise. The reaction was stirred at RT for 8 h. The reaction was washed with 1N HCl and extracted with DCM, dried with Na2SO4 and concentrated to give (2-chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-6-yl)methyl methanesulfonate (200 mg, yield: 80%). 1H-NMR (CDCl3, 400 MHz) δ 7.54 (d, J=8.0 Hz, 1H), 7.41 (s, 1H), 7.11˜7.20 (m, 3H), 6.79˜6.83 (m, 1H), 5.03˜5.08 (m, 1H), 4.06˜4.21 (m, 2H), 3.46˜3.52 (m, 1H), 3.24˜3.28 (m, 1H), 2.69 (s, 3H). MS (M+H)+: 381/383.

Workup

  1. stirringThe reaction was stirred at RT for 8 h
  2. washThe reaction was washed with 1N HCl
  3. extractionextracted with DCM
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b31d705b13074e8b9bb501ff49dbf8c6
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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