Cesium carbonate → 2,6-Dichloro-4-Cyano-N-{2-[(Cyclopropylcarbonyl)amino]pyridin-4-Yl}benzamide

HRID 449916

反応式

Br[C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:20])[C:10]2[C:15]([Cl:16])=[CH:14][C:13]([C:17]#[N:18])=[CH:12][C:11]=2[Cl:19])[CH:5]=[CH:4][N:3]=1.[CH:21]1([C:24]([NH2:26])=[O:25])[CH2:23][CH2:22]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Cl:19][C:11]1[CH:12]=[C:13]([C:17]#[N:18])[CH:14]=[C:15]([Cl:16])[C:10]=1[C:9]([NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:26][C:24]([CH:21]2[CH2:23][CH2:22]2)=[O:25])[CH:7]=1)=[O:20]

参加物

反応条件

温度: 140 °C

実験手順

A mixture of N-(2-bromopyridin-4-yl)-2,6-dichloro-4-cyanobenzamide (74 mg, 0.20 mmol), cyclopropanecarboxamide (34 mg, 0.40 mmol), Pd2(dba)3 (18 mg, 0.020 mmol), Xantphos (23 mg, 0.040 mmol), Cs2CO3 (131 mg, 0.40 mmol), dioxane (1.2 mL) was heated to 140° C. for 1 hour in a microwave reactor under nitrogen atmosphere. The mixture was filtered through Celite and then conentrated under reduced pressure. The residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to afford the desired product (30 mg, yield: 40%). 1H NMR (500 MHz, DMSO-d6): δ 11.28 (s, 1H), 10.79 (s, 1H), 8.36-8.24 (m, 4H), 7.47 (m, 1H), 2.00 (m, 1H), 0.81-0.79 (m, 4H). LCMS (ESI) m/z: 375 [M+H+].

後処理

filtrationThe mixture was filtered through Celite
customThe residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min)

出典と根拠

ORDレコード: ord-98de4c594b144a25a334c763f4709939
出典データセット: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08486950B2

反応式

参加物

反応物 4

生成物 1

試薬・触媒・溶媒 2

反応条件

実験手順

後処理

出典と根拠

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