Cesium carbonate → N-(2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl)cyclopropanecarboxamide

HRID 626654

反応式

HRID 626654 の反応式
Cl[C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=[C:6]2[CH:5]=[CH:4][N:3]=1.[CH:19]1([C:22]([NH2:24])=[O:23])[CH2:21][CH2:20]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+]>O1CCOCC1.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]>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[N:9]1[CH:8]=[C:7]2[C:2]([NH:24][C:22]([CH:19]3[CH2:21][CH2:20]3)=[O:23])=[N:3][CH:4]=[CH:5][C:6]2=[N:10]1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 80376CyclopropanecarboxamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866970364-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

生成物 1

HCID 69671224N-(2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl)cyclopropanecarboxamide収率 35%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

A suspension of 4-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (25 mg, 0.084 mmol), cyclopropanecarboxamide (16 mg, 0.19 mmol), Xantphos (14 mg, 0.024 mmol), Pd2(dba)3 (14 mg, 0.016 mmol) and Cs2CO3 (152 mg, 0.470 mmol) in dry dioxane (4.0 mL) was sealed in a microwave vial after degassing with nitrogen. The mixture was irradiated at 160° C. for 60 minutes in the microwave and then cooled to room temperature. The solid material was removed via filtration and the filtrate was purified via prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to afford N-(2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl)cyclopropanecarboxamide (10 mg, 35% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.19 (br, 1H), 8.90 (s, 1H), 7.99 (d, J=6.5 Hz, 1H), 7.79-7.67 (m, 3H), 7.39 (d, J=6.0 Hz, 1H), 2.13 (m, 1H), 0.92-0.86 (m, 4H). LCMS (Method A): RT=5.50 min, m/z: 347.0 [M+H+].

後処理

  1. customwas sealed in a microwave vial
  2. customafter degassing with nitrogen
  3. customThe mixture was irradiated at 160° C. for 60 minutes in the microwave
  4. customThe solid material was removed via filtration
  5. customthe filtrate was purified via 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-785056e2441a4315af3de8ec18e8ec64
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

関連ノート

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