4-Methoxybenzylamine → [2,3-Difluoro-6-(4-methoxy-benzylamino)-pyridin-4-yl]-methanol

HRID 426229Notes

Reaction equation

HRID 426229 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([CH2:9][OH:10])[CH:5]=[C:4](F)[N:3]=1.[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1>>[F:1][C:2]1[C:7]([F:8])=[C:6]([CH2:9][OH:10])[CH:5]=[C:4]([NH:19][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[N:3]=1

Participants

3

Reactant 2

HCID 754524-MethoxybenzylamineHCID 22392087(2,3,6-Trifluoropyridin-4-yl)methanol

Product 1

HCID 59184869[2,3-Difluoro-6-(4-methoxy-benzylamino)-pyridin-4-yl]-methanolYield 94.9%

Procedure

To a 100 ml round bottomed flask, were placed (2,3,6-trifluoro-pyridin-4-yl)-methanol (515 mg, 3.15 mmol) and p-methoxybenzyl amine (1.0 ml, 7.57 mmol). Nitrogen balloon was attached to the flask and the mixture was stirred in an oil bath (117˜130° C.) for 2.5 hr. After cooling to room temperature, the mixture was purified by silica gel column chromatography (eluent, dichloromethane: methanol (95:5)) to afford 838 mg (94%) of [2,3-difluoro-6-(4-methoxy-benzylamino)-pyridin-4-yl]-methanol as a pale brown solid. 1H NMR (200 MHz, CDCl3) δ 2.04 (1H, br. s), 3.79 (3H, s), 4.52 (2H, d, J=5.6 Hz), 4.70 (2H, br. s), 4.84 (1H, br. s), 6.22 (1H, m), 6.83-6.90 (2H, m), 7.24-7.31 (2H, m).

Workup

  1. customTo a 100 ml round bottomed flask, were placed
  2. customthe mixture was purified by silica gel column chromatography (eluent, dichloromethane: methanol (95:5))

Sources & evidence

ORD record
ord-9f0ca43119654e888c08ad98984ae983
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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