Potassium Cyanide → HCID 67005777, compound

HRID 563370Notes

Reaction equation

HRID 563370 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4([C:23]([CH3:29])([CH3:28])[C:24]([O:26]C)=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[C-]#N.[K+].[Li+].[I-]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4([C:23]([CH3:29])([CH3:28])[C:24]([OH:26])=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 66321Lithium iodideHCID 59252780HCID 59252780, compound

Product 1

HCID 67005777HCID 67005777, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
180 °C

Procedure

Methyl 2-(1-(1-(4-fluorophenyl)-1H-indazol-5-yl)cyclohexyl)-2-methylpropanoate (635 mg, 1.61 mmol) was dissolved in 4 mL pyridine and transferred to a microwave reactor. Potassium cyanide (419 mg, 6.45 mmol) and LiI (864 mg, 6.45 mmol) were added and the reactor was sealed under nitrogen and heated in a microwave for 30 min at 180° C. The reaction was extracted from 1 M HCl using EtOAc×4 (lots of black, insoluble precipitate). The organic layers were dried, concentrated, and purified by MPLC on SiO2 using 1:1 EtOAc/hexanes. Obtained 115 mg (19%) of off white powder 2-(1-(1-(4-fluorophenyl)-1H-indazol-5-yl)cyclohexyl)-2-methylpropanoic acid.

Workup

  1. customtransferred to a microwave reactor
  2. customthe reactor was sealed under nitrogen
  3. extractionThe reaction was extracted from 1 M HCl
  4. customThe organic layers were dried
  5. concentrationconcentrated
  6. custompurified by MPLC on SiO2 using 1:1 EtOAc/hexanes

Sources & evidence

ORD record
ord-4418ec81b0cb41ef9b7f1152c0dd589b
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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