2-Amino-5-bromo-3-methylpyridine → 3-Methyl-5-(4-trifluoromethyl-phenyl)-pyridin-2-ylamine

HRID 1784566Notes

Reaction equation

HRID 1784566 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](Br)=[CH:4][N:3]=1.[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1>>[CH3:8][C:7]1[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([C:15]2[CH:16]=[CH:17][C:12]([C:11]([F:22])([F:21])[F:10])=[CH:13][CH:14]=2)[CH:6]=1

Participants

3

Reactant 2

HCID 1379342-Amino-5-bromo-3-methylpyridineHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 666505703-Methyl-5-(4-trifluoromethyl-phenyl)-pyridin-2-ylamineYield 88.2%

Procedure

Prepared as described in example C.32 (step 4) from commercially available 2-amino-5-bromo-3-methyl-pyridine (4.5 g, 24.1 mmol) and commercially available 4-trifluoromethyl-phenylboronic acid (5.03 g, 26.5 mmol). Obtained as an off-white solid (5.36 g, 88%). MS (ISP) 252.9 [(M+H)+]; mp 159° C.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-1199af4504b547a281d8fc4822f31bea
Source dataset
uspto-grants-2009_03
Patent number
US07504404B2

Reaction notes

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