Hydrochloric Acid → 5-Iodo-3-methyl-9H-pyrido[2,3-b]indole-7-carbonitrile

HRID 1882231Notes

Reaction equation

N[C:2]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[C:7]2[C:3]=1[C:4]1[CH:16]=[C:15]([CH3:17])[CH:14]=[N:13][C:5]=1[NH:6]2.Cl.N([O-])=O.[Na+].[I:23]I.[I-].[K+]>CC(O)=O.O>[I:23][C:2]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[C:7]2[C:3]=1[C:4]1[CH:16]=[C:15]([CH3:17])[CH:14]=[N:13][C:5]=1[NH:6]2

Participants

Conditions

Temperature: 0 °C

Procedure

Compound 124 (118 mg, 0.53 mmol) was dissolved in HOAc (2 mL) with H2O (1 mL), and the solution stirred at 0° C. Concentrated HCl (120 μL) in H2O (120 mL) was added, and the reaction stirred for 5 min. Sodium nitrite (54 mg, 0.78 mmol) in H2O (120 μL) was added dropwise, and the red solution stirred for 10 min. A solution of iodine (10 mg) and potassium iodide (129 mg, 0.78 mmol) in H2O (300 μL) was added dropwise, and the brown frothy solution stirred for 30 min at 0° C. and then 30 min while warming to r.t. The reaction was diluted with H2O (5 mL) and extracted with CHCl3. Organics were dried (MgSO4) and concentrated in vacuo. Purification by silica gel chromatography gave 108 mg (61%) of the title compound as a faintly yellow solid. MS (ES) [m+H] calc'd for C13H8IN3, 334; found 334.

Workup

stirringthe reaction stirred for 5 min
stirringthe red solution stirred for 10 min
stirringthe brown frothy solution stirred for 30 min at 0° C.
temperature30 min while warming to r.t
extractionextracted with CHCl3
dry with materialOrganics were dried (MgSO4)
concentrationconcentrated in vacuo
customPurification by silica gel chromatography

Sources & evidence

ORD record: ord-989287a9ece5442b937e28f96aafe3bd
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318939B2

Reaction notes

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