Potassium Cyanide → HCID 67167406, Verbindung

HRID 874714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 874714
ClC(Cl)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])=[CH:8][C:7]=1[C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2([C:29]([F:32])([F:31])[F:30])[N:28]=[N:27]2)=[CH:22][CH:21]=1)=[O:19])=O.[C-]#[N:35].[K+]>CCO.O>[NH2:35][C:3]1[C:18]([C:20]2[CH:21]=[CH:22][C:23]([C:26]3([C:29]([F:32])([F:31])[F:30])[N:28]=[N:27]3)=[CH:24][CH:25]=2)([OH:19])[C:7]2[C:6](=[CH:11][CH:10]=[C:9]([C:12]#[C:13][Si:14]([CH3:15])([CH3:16])[CH3:17])[CH:8]=2)[N:5]=1

Komponenten

5

Edukt 2

HCID 9032Potassium CyanideHCID 67167119HCID 67167119, Verbindung

Produkt 1

HCID 67167406HCID 67167406, VerbindungAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

2,2-dichloro-N-[2-({4-[3-(trifluoromethyl)diazirin-3-yl]phenyl}carbonyl)-4-[2-(trimethylsilyl)ethynyl]phenyl]acetamide (57 mg, 0.11 mmol, 1 eq.) was dissolved in EtOH (3 mL). Potassium cyanide (9.4 mg, 0.14 mmol, 1.3 eq.) in water (1 mL) was added to the reaction, and the reaction was stirred at room temperature for 16 hours. The EtOH was evaporated, and additional water (8 mL) was added. The reaction was then extracted three times with 5% isopropanol in DCM (20 mL each), and the organic layer was dried over sodium sulfate. The solvent was evaporated, and the residue was purified on silica column (DCM/MeOH, 39:1→19:1→9:1→4:1) to result in 39.2 mg (82%) of the title compound as a yellow solid. 1H NMR (500 MHz, CD3OD) δ 7.44 (d, J=8.5, 2H, Ar—H), 7.29 (dd, J=1.8, 8.8, 1H, Ar—H), 7.22 (d, J=8.3, 2H, Ar—H), 7.02-6.94 (m, 2H, Ar—H), 0.18 (s, 9H, SiC3H9). 13C NMR (126 MHz, CD3OD) δ 180.56 (C—NH2), 156.85 (C—Ar), 144.59 (C—Ar), 140.89 (C—Ar), 135.13 (C—Ar), 129.58 (C—Ar), 127.89 (d, J=0.88, C—Ar), 127.66 (C—Ar), 126.99 (C—Ar), 123.70 (q, J=273.80, CF3), 117.82 (C—Ar), 116.69 (C—Ar), 107.08 (CSi(CH3)3), 92.94 (CCSi(CH3)3), 84.20 (Ar—COH), 29.55 (q, J=40.25, CN2), 0.23 (Si(CH3)3). Exact Mass, 428.13.

Aufarbeitung

  1. customThe EtOH was evaporated
  2. additionadditional water (8 mL) was added
  3. extractionThe reaction was then extracted three times with 5% isopropanol in DCM (20 mL each)
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified on silica column (DCM/MeOH, 39:1→19:1→9:1→4:1)

Quellen und Nachweise

ORD-Eintrag
ord-3fecae9254044482bb70d87040a82d7a
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980926B2

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