Triethylamine → HCID 86723309, compound

HRID 2366218Notes

Reaction equation

[Cl:1][C:2]1[C:7]([F:8])=[C:6]([NH2:9])[CH:5]=[CH:4][N:3]=1.[Cl:10][C:11]1[CH:19]=[C:18]([I:20])[CH:17]=[C:16]([Cl:21])[C:12]=1[C:13](Cl)=[O:14].C(N(CC)CC)C>O1CCOCC1>[Cl:10][C:11]1[CH:19]=[C:18]([I:20])[CH:17]=[C:16]([Cl:21])[C:12]=1[C:13]([NH:9][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=1[F:8])=[O:14]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-chloro-3-fluoropyridin-4-ylamine (1.73 g, 11.8 mmol), 2,6-dichloro-4-iodobenzoyl chloride (5.90 g, 17.65 mmol) and triethylamine (3.1 mL, 22.4 mmol) in dioxane (35 mL) was heated to 100° C. for 18 hours. The reaction mixture was partitioned between EtOAc and water. The organic layer washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The resultant residue was triturated with diethyl ether and dried under reduced pressure to give the desired compound as a pink solid (2.83 g, 54% yield). 1H NMR (300 MHz, CDCl3): δ 8.49-8.43 (m, 1H), 8.22 (d, J=5.5 Hz, 1H), 7.82-7.73 (m, 2H).

Workup

customThe reaction mixture was partitioned between EtOAc and water
washThe organic layer washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe resultant residue was triturated with diethyl ether
customdried under reduced pressure

Sources & evidence

ORD record: ord-5332521f85cb41eaaf7bc9d0707d3299
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697708B2

Reaction notes

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