Trichloroacetonitrile → HCID 57546209, compound

HRID 913833Notes

Reaction equation

[Br:1][C:2]1[N:3]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[N:4]=[C:5]2[C:10]=1[CH:9]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:7]=[C:6]2[CH:15]([OH:17])[CH3:16].N12CCCN=C1CCCCC2.[Cl:37][C:38]([Cl:42])([Cl:41])[C:39]#[N:40]>C(OCC)C>[Cl:37][C:38]([Cl:42])([Cl:41])[C:39](=[NH:40])[O:17][CH:15]([C:6]1[C:5]2[C:10](=[C:2]([Br:1])[N:3]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:24])([CH3:23])[CH3:25])[N:4]=2)[CH:9]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:7]=1)[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

(±)-1-(3-Bromo-5-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)ethanol (1.07 g, 2.44 mmol) was dissolved in diethyl ether (10 mL), cooled to 0° C. and treated with 1,8-diazabicyclo(5.4.0)undec-7-ene (70 μL, 0.49 mmol). The reaction was stirred for 10 min and treated with trichloroacetonitrile (370 μL, 3.65 mmol) dropwise over 10 min. The reaction was allowed to warm to room temperature overnight and concentrated. Flash chromatography on silica gel (5% ethyl acetate/hexanes) gave 1.29 g (91%) as an oil. 1H-NMR (CDCl3, 300 MHz) δ 8.25 (s, 1H), 7.86 (s, 1H), 6.66 (q, J=6.6 Hz, 1H), 6.27 (d, J=11.7 Hz, 1H), 5.68 (d, J=11.7 Hz, 1H), 3.52-3.59 (m, 2H), 1.77 (d, J=6.6 Hz, 3H), 0.82-0.87 (m, 2H), 0.05 (s, 9H).

Workup

temperatureto warm to room temperature overnight
concentrationconcentrated
customFlash chromatography on silica gel (5% ethyl acetate/hexanes) gave 1.29 g (91%) as an oil

Sources & evidence

ORD record: ord-b7523af702c542558d7320ab1205c490
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026257B2

Reaction notes

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