Acetonitrile → HCID 86696503, compound

HRID 1615904Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(#N)C.C(N(CC)CC)C>N1C=CC=CC=1>[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([NH:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 2,4-dichloro-3-(trifluoromethyl)pyridine (197 mg, 0.912 mmol) and 3-aminopropylbenzene (0.136 mL, 0.925 mmol) was added acetonitrile (8.0 mL) and triethylamine (0.153 mL, 1.095 mmol). The mixture was heated to 80° C. After five hours the mixture was removed from heat and concentrated. This material was purified on silica gel (25 g) equilibrated in hexane, loaded in dichloromethane and eluted using hexane (96 mL) 0 to 30% EtOAc/hexane (600 mL, linear gradient). Early eluting fractions gave 51 mg of a pale yellow film as a 1:1 mixture of the minor 2-isomer and pyridine starting material by 1H NMR. Later eluting fractions gave 172 mg of a pale yellow film. This was consistent with the desired product by 1H NMR (400 MHz, CHLOROFORM-d) δ 8.02 (d, J=6.0 Hz, 1H), 7.37-7.29 (m, 2H), 7.27-7.17 (m, 3H), 6.45 (d, J=6.0 Hz, 1H), 5.52-5.31 (m, 1H), 3.27-3.16 (m, 2H), 2.75 (t, J=7.4 Hz, 2H), 2.02 (quin, J=7.3 Hz, 2H).

Workup

customAfter five hours the mixture was removed
temperaturefrom heat
concentrationconcentrated
customThis material was purified on silica gel (25 g)
washeluted
customEarly eluting fractions gave 51 mg of a pale yellow film
washLater eluting fractions
customgave 172 mg of a pale yellow film

Sources & evidence

ORD record: ord-91e0779faf7a4b889a75a51f5bb0aef6
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765767B2

Reaction notes

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