2-Fluoro-4-iodoaniline → 5-[(2-Fluoro-4-iodophenyl)amino]-2-methylisonicotinic acid

HRID 2421665

Reaction equation

HRID 2421665 reaction equation
F[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]([CH3:11])=[N:4][CH:3]=1.[F:12][C:13]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][C:14]=1[NH2:15].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>>[F:12][C:13]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][C:14]=1[NH:15][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]([CH3:11])=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 1856942-Fluoro-4-iodoanilineHCID 2733832Lithium HexamethyldisilazideHCID 576496205-Fluoro-2-methylisonicotinic acid

Product 1

HCID 115016085-[(2-Fluoro-4-iodophenyl)amino]-2-methylisonicotinic acid

Procedure

5-[(2-fluoro-4-iodophenyl)amino]-2-methylisonicotinic acid was synthesized according to the general procedure of Method 1 as, outlined above, starting with 200 mg (1.29 mmol) of 5-fluoro-2-methylisonicotinic acid, 370 mg (1.55 mmol) of 2-fluoro-4-iodoaniline and two portions of lithium bis(trimethylsilyl)amide (3.35 ml, 3.35 mmol), and (1.55 ml, 1.55 mmol). Yield: 30 mg, 6%, LC/MS [5.5 min; 473 (M+1)]

Workup

  1. customYield: 30 mg, 6%, LC/MS [5.5 min; 473 (M+1)]

Sources & evidence

ORD record
ord-ea56ce10992d4d25ae4f834a4264afef
Source dataset
uspto-grants-2011_06
Patent number
US07956191B2

Linked notes

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