4-Methoxybenzylamine → N-(4-methoxybenzyl)(2-(2-fluoro-6-methoxyphenyl)-8-methylquinolin-3-yl)methanamine

HRID 216767Notes

Reaction equation

HRID 216767 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[C:19]([CH:20]=O)=[CH:18][C:17]2[C:12](=[C:13]([CH3:22])[CH:14]=[CH:15][CH:16]=2)[N:11]=1.[CH2:23]([NH2:32])[C:24]1[CH:31]=[CH:30][C:27]([O:28][CH3:29])=[CH:26][CH:25]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH3:29][O:28][C:27]1[CH:30]=[CH:31][C:24]([CH2:23][NH:32][CH2:20][C:19]2[C:10]([C:3]3[C:4]([O:8][CH3:9])=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:22])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 754524-MethoxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 577078192-(2-Fluoro-6-methoxyphenyl)-8-methylquinoline-3-carbaldehyde

Product 1

HCID 57707905N-(4-methoxybenzyl)(2-(2-fluoro-6-methoxyphenyl)-8-methylquinolin-3-yl)methanamine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Prepared according to Procedure F using 2-(2-fluoro-6-methoxyphenyl)-8-methylquinoline-3-carbaldehyde (1.086 g, 3.68 mmol), DCE (18 mL), PMBNH2 (0.95 mL, 7.36 mmol, 2.0 eq), and NaBH(OAc)3 (2.3387 g, 11.03 mmol, 3 eq) After purification, N-(4-methoxybenzyl)(2-(2-fluoro-6-methoxyphenyl)-8-methylquinolin-3-yl)methanamine was obtained as yellow syrup. 1H NMR (DMSO-d6) δ ppm 8.42 (1H, s), 7.84 (1H, d, J=7.4 Hz), 7.55-7.62 (1H, m), 7.43-7.54 (2H, m), 7.13 (2H, d, J=8.6 Hz), 6.90-7.01 (2H, m), 6.77-6.85 (2H, m), 3.71 (3H, s), 3.65 (3H, s), 3.47-3.62 (4H, m), 2.64 (3H, s), 2.43 (1H, s). Mass Spectrum (ESI) m/e=417.3 (M+1).

Workup

  1. customPrepared
  2. customAfter purification

Sources & evidence

ORD record
ord-c696591aae054688a9e7d9c57bcf313e
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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