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Potassium Carbonate → N-(tert-butyl)-5-(1-chloro-8-phenylpyrrolo[1,2-d][1,2,4]triazin-4-yl)pyridine-3-sulfonamide

HRID 1478401
ノート
印刷プレビュー

反応式

HRID 1478401 の反応式
[Cl:1][C:2]1[C:3]2[N:4]([CH:9]=[CH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5](Cl)=[N:6][N:7]=1.[C:18]([NH:22][S:23]([C:26]1[CH:27]=[N:28][CH:29]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:31]=1)(=[O:25])=[O:24])([CH3:21])([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:18]([NH:22][S:23]([C:26]1[CH:27]=[N:28][CH:29]=[C:30]([C:5]2[N:4]3[CH:9]=[CH:10][C:11]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[C:3]3[C:2]([Cl:1])=[N:7][N:6]=2)[CH:31]=1)(=[O:25])=[O:24])([CH3:21])([CH3:19])[CH3:20]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 90386425N-(tert-Butyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamideHCID 904252191,4-Dichloro-8-phenylpyrrolo[1,2-d][1,2,4]triazine

生成物 1

HCID 90425182N-(tert-butyl)-5-(1-chloro-8-phenylpyrrolo[1,2-d][1,2,4]triazin-4-yl)pyridine-3-sulfonamide収率 32%

試薬・触媒・溶媒 3

HCID 178418476
HCID 178418476、化合物
触媒
HCID 962Water溶媒2 回
HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of 1,4-dichloro-8-phenylpyrrolo[1,2-d][1,2,4]triazine (0.150 g, 0.568 mmol) in 1,4-dioxane (15 mL) and water (4 mL) was added N-(tert-butyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamide (prepared according to WO 2011/028741) (0.232 g, 0.682 mmol) followed by potassium carbonate (0.235 g, 1.70 mmol) The reaction mixture was purged with N2 for 30 min. Bis(triphenylphosphine)palladium(II) chloride (20.0 mg, 0.0280 mmol) was added to the reaction mixture and heated at 100° C. in a sealed tube for 12 h. The reaction mixture was allowed to cool and filtered through a pad of CELITE®. The filtrate was concentrated under reduced pressure to give a residue which was suspended in water (100 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure to give a residue which was purified by silica gel column chromatography using CombiFlash (REDISEP®, silica gel, 12 g, 30% EtOAc/hexanes) to yield N-(tert-butyl)-5-(1-chloro-8-phenylpyrrolo[1,2-d][1,2,4]triazin-4-yl)pyridine-3-sulfonamide (80.0 mg, 32.0%) as a pale yellow liquid. LCMS Method B-3: retention time 2.07 min, [M+1]=442.0. 1H NMR (400 MHz, DMSO-d6) δ ppm: 1.19 (s, 9H), 7.23 (d, J=3.2 Hz, 1H), 7.42-7.55 (m, 5H), 7.90 (d, J=3.2 Hz, 1H), 8.00 (br s, 1H), 8.73 (t, J=2.0 Hz, 1H), 9.17 (d, J=2.0 Hz, 1H), 9.22 (d, J=2.0 Hz, 1H).

後処理

  1. customwas purged with N2 for 30 min
  2. temperatureto cool
  3. filtrationfiltered through a pad of CELITE®
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give a residue which
  6. extractionextracted with ethyl acetate (3×50 mL)
  7. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  8. customevaporated under reduced pressure
  9. customto give a residue which
  10. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-a9218009c5f147a69b6ad5d778f8da4b
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09403834B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート