Toluene → HCID 86715512, compound

HRID 2284599Notes

Reaction equation

HRID 2284599 reaction equation
[N:1]#[C:2]Br.[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([C:17]3[CH:18]=[N:19][C:20]([CH2:23][NH2:24])=[CH:21][CH:22]=3)=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:7][C:6]=1[CH3:25].CCN(C(C)C)C(C)C.C1(C)C=CC=CC=1>C(#N)C>[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]4[N:19]([C:2]([NH2:1])=[N:24][CH:23]=4)[CH:18]=3)=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:7][C:6]=1[CH3:25]

Participants

6

Reactant 4

HCID 1140TolueneHCID 10476Cyanogen BromideHCID 81531DiisopropylethylamineHCID 86715505HCID 86715505, compound

Product 1

HCID 86715512HCID 86715512, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Cyanogen bromide (62 mg) in dry acetonitrile (1 mL) was added to a screw capped vial containing a stirring solution of (2′-(4-fluoro-3-methylphenyl)-[3,3′-bipyridin]-6-yl)methanamine.xHCl (120 mg), i-Pr2NEt (0.2 mL) and anhydrous toluene. After 4 h, the reaction mixture was concentrated and purified by reverse phase preparative HPLC conditions provided 6-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)imidazo[1,5-a]pyridin-3-amine (28 mg).

Workup

  1. customcapped vial
  2. concentrationthe reaction mixture was concentrated
  3. custompurified by reverse phase preparative HPLC conditions

Sources & evidence

ORD record
ord-a6a7dd8d792e4b43a5a38e3d4cbfefb4
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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