Triethylamine → (5-Chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)methyl methanesulfonate

HRID 913914Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]([CH2:11][OH:12])[C:8]2[C:4](=[CH:5][N:6]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:7]=2)[CH:3]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl>[CH3:28][S:29]([O:12][CH2:11][C:9]1[C:8]2[C:4](=[CH:5][N:6]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:7]=2)[CH:3]=[C:2]([Cl:1])[CH:10]=1)(=[O:31])=[O:30]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)methanol (2.5 g, 8 mmol) and triethylamine (3.34 mL, 24 mmol) in dichloromethane (120 mL) at 0° C. was added methanesulfonyl chloride (1.25 mL, 16 mmol). The reaction was stirred at 0° C. for 1 h. The reaction was quenched by addition of water, stirred 5 min, and poured into water. The layers were separated and the organics washed with brine, dried over magnesium sulfate, and concentrated to give 3.25 g (quant.). 1H-NMR (CDCl3, 500 MHz) δ 8.09 (s, 1H), 7.66 (d, J=1.8 Hz, 1H), 7.31 (d, J=0.9 Hz, 1H), 5.68 (s, 2H), 5.59 (s, 2H), 3.60 (t, J=8.2 Hz, 2H), 3.06 (s, 3H), 0.91 (t, J=8.2 Hz, 2H), −0.05 (s, 9H); 13C NMR (126 MHz, CDCl3) δ ppm 145.4, 127.5, 127.4, 125.0, 123.0, 122.8, 120.5, 82.1, 67.8, 67.4, 38.0, 17.9, −1.4. Mass spec.: 391.14 (MH)+.

Workup

customThe reaction was quenched by addition of water
stirringstirred 5 min
additionpoured into water
customThe layers were separated
washthe organics washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customto give 3.25 g (quant.)

Sources & evidence

ORD record: ord-d34bb360c99b43cbbb179930876d7a62
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026257B2

Reaction notes

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