Trichloroacetonitrile → HCID 57546044, compound

HRID 913868Notes

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]([CH:11]([OH:13])[CH3:12])[C:8]2[C:4](=[CH:5][N:6]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:7]=2)[CH:3]=1.N12CCCN=C1CCCCC2.[Cl:33][C:34]([Cl:38])([Cl:37])[C:35]#[N:36]>ClCCl>[Cl:33][C:34]([Cl:38])([Cl:37])[C:35](=[NH:36])[O:13][CH:11]([C:9]1[C:8]2[C:4](=[CH:5][N:6]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:20])([CH3:19])[CH3:21])[N:7]=2)[CH:3]=[C:2]([F:1])[CH:10]=1)[CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

(±)-1-(5-Fluoro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)ethanol (1.58 g, 5.09 mmol) was dissolved in dichloromethane (10 mL), cooled to 0° C. and treated with 1,8-diazabicyclo(5.4.0)undec-7-ene (153 μL, 1.018 mmol). The reaction was stirred for 10 min and treated with trichloroacetonitrile (5.1 mL, 50.9 mmol) dropwise over 10 min. The reaction was stirred at room temperature for 2 h and concentrated. The resulting residue was dissolved in diethyl ether. The resulting solution was decanted to separate it from the resulting dark tar which formed. The ethereal was concentrated to give 2.247 g (97%). 1H-NMR (CDCl3, 300 MHz) δ 8.35 (s, 1H), 8.03 (s, 1H), 7.16 (m, 1H), 6.63 (q, J=6.0 Hz, 1H), 5.68 (s, 2H), 3.62 (m, 2H), 1.78 (d, J=6.0 Hz, 3H), 0.89-0.94 (m, 2H), −0.05 (s, 9H).

Workup

stirringThe reaction was stirred at room temperature for 2 h
concentrationconcentrated
dissolutionThe resulting residue was dissolved in diethyl ether
customThe resulting solution was decanted
customto separate it from the resulting dark tar which
customformed
concentrationThe ethereal was concentrated
customto give 2.247 g (97%)

Sources & evidence

ORD record: ord-d5e9686cd1574e148dd30c5acdea85eb
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026257B2

Reaction notes

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