Trichloroacetonitrile → HCID 57545938, compound

HRID 913818Notes

Reaction equation

HRID 913818 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:11]=[C:10]([CH:12]([OH:14])[CH3:13])[C:9]2[C:5](=[CH:6][N:7]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:8]=2)[CH:4]=1.[Cl:25][C:26]([Cl:30])([Cl:29])[C:27]#[N:28].N12CCCN=C1CCCCC2>ClCCl>[Cl:25][C:26]([Cl:30])([Cl:29])[C:27](=[NH:28])[O:14][CH:12]([C:10]1[C:9]2[C:5](=[CH:6][N:7]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:20])([CH3:22])[CH3:21])[N:8]=2)[CH:4]=[C:3]([C:2]([F:1])([F:23])[F:24])[CH:11]=1)[CH3:13]

Participants

5

Reactant 3

HCID 11011TrichloroacetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57546130HCID 57546130, compound

Product 1

HCID 57545938HCID 57545938, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-1-(5-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)ethanol (2.5 g, 6.94 mmol) and trichloroacetonitrile (6.95 mL, 69.4 mmol) in dichloromethane (50 mL) at room temperature was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.1 mL, 0.66 mmol). After stirring for 4 h, the reaction was concentrated and purified by column chromatography (12% EtOAc/Hex+0.1% Et3N) to give 3.1 g, (89%) as a white powder. 1H-NMR (CDCl3, 500 MHz) δ 8.33 (s, 1H), 8.22 (s, 1H), 7.95 (s, 1H), 7.57 (s, 1H), 6.67 (q, J=6.6 Hz, 1H), 5.73 (s, 2H), 3.65 (t, J=8.4 Hz, 2H), 1.80 (d, J=6.6 Hz, 3H), 0.93 (m, 2H), −0.05 (s, 9H). Mass spec.: 526.90 (MH)+.

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified by column chromatography (12% EtOAc/Hex+0.1% Et3N)
  3. customto give 3.1 g, (89%) as a white powder

Sources & evidence

ORD record
ord-dd371b092e1a426fa3573c15df847394
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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