Cesium carbonate → Methyl 4-(8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoate

HRID 57769

反応式

[Br:1][C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH2:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.I[C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH:11][C:13]3[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1

参加物

反応条件

温度: 80 °C

実験手順

A suspension of 8-bromo-[1,2,4]triazolo[1, 5-a]pyridin-2-amine (2.8 g, 13.2 mmol, 1 equiv), methyl 4-iodobenzoate (3.4 g, 13 mmol, 1.0 equiv), cesium carbonate (8.4 g, 26 mmol, 2.0 equiv), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (763 mg, 1.32 mmol, 0.10 equiv), and palladium (II) acetate (300 mg, 1.32 mmol, 0.10 equiv) in dioxane (100 mL) was heated at 80° C. for 1 h. The reaction mixture was cooled to room temperature and diluted with dichloromethane (100 mL). The resulting solids were filtered and sequentially rinsed with water (3×50 mL) and methanol (2×20 mL). The solids were dried in vacuo to afford methyl 4-(8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoate (3.1 g). 1H NMR (400 MHz, DMSO-d6), δ: 10.42 (s, 1H), 8.87 (m, 1H), 7.93 (m, 1H), 7.92 (d, J=8.8 Hz, 2H), 7.77 (d, J=8.8 Hz, 2H), 7.00 (dd, J=7.4, 6.9 Hz, 1H), 3.81 (s, 3H).

後処理

temperatureThe reaction mixture was cooled to room temperature
filtrationThe resulting solids were filtered
washsequentially rinsed with water (3×50 mL) and methanol (2×20 mL)
customThe solids were dried in vacuo

出典と根拠

ORDレコード: ord-70c2d067330c483b97778b370d71ce27
出典データセット: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US09434732B2

反応式

参加物

反応物 4

生成物 1

試薬・触媒・溶媒 3

反応条件

実験手順

後処理

出典と根拠

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