2-chloro-N,N-dimethylacetamide → 2-[2-fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenoxy]-N,N-dimethylacetamide

HRID 1061834Notes

Reaction equation

HRID 1061834 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[N:13][C:14]([C:18]([F:21])([F:20])[F:19])=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[OH:22].Cl[CH2:24][C:25]([N:27]([CH3:29])[CH3:28])=[O:26]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[N:13][C:14]([C:18]([F:19])([F:20])[F:21])=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[O:22][CH2:24][C:25]([N:27]([CH3:29])[CH3:28])=[O:26]

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 222853142-Fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenol

Product 1

HCID 102718712-[2-fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenoxy]-N,N-dimethylacetamideYield 58.5%

Procedure

2-Fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenol (50.0 mg, 0.16 mmol) was alkylated with 2-chloro-N,N-dimethylacetamide (20.1 μL, 23.7 mg, 0.20 mmol) as described in Example 47, affording 2-[2-fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenoxy]-N,N-dimethylacetamide (36.8 mg, 58%). δH (360 MHz, CDCl3) 2.99 (3H, s), 3.10 (3H, s), 4.85 (2H, s), 7.05-7.09 (1H, m), 7.18 (1H, dd, J 2.1 and 8.1), 7.31 (1H, dd, J 8.1 and 10.9), 7.54 (1H, d, J 4.2), 7.82 (1H, d, J 8.4), 8.53 (1H, d, J 8.4), 9.25 (1H, d, J 4.6). m/z (ES+) 394 [MH]+.

Sources & evidence

ORD record
ord-cd706c32c3fd40989afbb898ad4a4dce
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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