Water → 6-Fluoro-4-[(3-isopropylphenyl)amino]-1,7-naphthyridine-3-carbonitrile

HRID 2113573Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]#[N:14].[CH:15]([C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21])([CH3:17])[CH3:16].O>C(O)C>[F:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][N:8]=1)[N:5]=[CH:4][C:3]([C:13]#[N:14])=[C:2]2[NH:21][C:20]1[CH:22]=[CH:23][CH:24]=[C:18]([CH:15]([CH3:17])[CH3:16])[CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-chloro-6-fluoro-[1,7]naphthyridine-3-carbonitrile (0.75 g, 3.62 mmol) and 3-isopropylaniline (0.82 mL, 5.79 mmol) in ethanol (11 mL) was heated to 80° C. for 10 hours. The reaction was cooled to 0° C., water was added and the mixture was stirred for 15 minutes. The product was filtered, washed with water and dried in the vacuum oven to provide pure 6-fluoro-4-[(3-isopropylphenyl)amino]-1,7-naphthyridine-3-carbonitrile (0.88 g, 80%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.2 (d, J=7.1 Hz, 6 H) 2.9 (dq, J=6.9 Hz, 1 H) 7.2 (m, 3 H) 7.4 (t, J=7.8 Hz, 1 H) 8.2 (s, 1 H) 8.6 (s, 1 H) 9.1 (s, 1 H) 10.1 (s, 1 H).

Workup

filtrationThe product was filtered
washwashed with water
customdried in the vacuum oven

Sources & evidence

ORD record: ord-3f98520c539a461cbca53f2b137ea30f
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432279B2

Reaction notes

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