Methanesulfonyl chloride → 3-(1-Methyl-3-indolyl)-1-propyl methanesulfonate

HRID 50993Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH2:12][CH2:13][OH:14])=[CH:3]1.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>>[CH3:15][S:16]([O:14][CH2:13][CH2:12][CH2:11][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([CH3:1])[CH:3]=1)(=[O:18])=[O:17]

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 227358873-(1-Methyl-1H-indol-3-yl)propan-1-ol

Product 1

HCID 227354863-(1-Methyl-3-indolyl)-1-propyl methanesulfonate

Procedure

3-(1-methyl-3-indolyl)-1-propyl methanesulfonate was prepared by following the general procedure of Example 43 for mesylation as a colorless oil (291 mg, 84%) from 3-(1-methyl-3-indolyl)-1-propanol (245 mg, 1.30 mmol) and methanesulfonyl chloride (223 mg, 1.94 mmol). 1H NMR (CDCl3, 300 MHz) δ2.15 (qu, 2H, J=7.0 Hz), 2.90 (t, 2H, J=7.0 Hz), 2.99 (s, 3H), 3.76 (s, 3H), 4.27 (t, 2H, J=6.2 Hz), 6.88 (s, 1H), 7.11 (dt, 1H, J=1.1, 6.9 Hz), 7.23 (dt, 1H, J=1.1, 7.0 Hz), 7.29 (d, 1H, J=8.5 Hz), 7.57 (d, 1H, J=8.1 Hz) ppm.

Sources & evidence

ORD record: ord-f4f32b411034435d973de1d0e728886f
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713471B1

Reaction notes

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