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Cesium carbonate → 1-methyl-N-(1-methyl-3-(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazole-3-sulfonamide

HRID 331068
ノート
印刷プレビュー

反応式

HRID 331068 の反応式
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:22])[CH:9]=[C:10]([C:11]3[CH:21]=[CH:20][C:14]4[O:15][CH2:16][CH2:17][N:18]([CH3:19])[C:13]=4[CH:12]=3)[C:3]=12.[CH3:23][N:24]1[CH:28]=[CH:27][C:26]([S:29]([NH2:32])(=[O:31])=[O:30])=[N:25]1.CN(C)C1C=CC=CC=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.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]>[CH3:23][N:24]1[CH:28]=[CH:27][C:26]([S:29]([NH:32][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[N:8]([CH3:22])[CH:9]=[C:10]([C:11]4[CH:21]=[CH:20][C:14]5[O:15][CH2:16][CH2:17][N:18]([CH3:19])[C:13]=5[CH:12]=4)[C:3]=23)(=[O:31])=[O:30])=[N:25]1
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 4

HCID 10796Cesium carbonateHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 148356431-methyl-1H-pyrazole-3-sulfonamideHCID 710901456-(4-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine

生成物 1

HCID 867202961-methyl-N-(1-methyl-3-(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazole-3-sulfonamide
収率 22%

試薬・触媒・溶媒 2

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

反応条件

温度
120 °C

実験手順

Alternatively, a mixture of 6-(4-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine (130 mg, 0.363 mmol), 1-methyl-1H-pyrazole-3-sulfonamide (D94) (88 mg, 0.544 mmol), 2-(dimethylamino)-2′-(dicyclohexylphosphino)biphenyl (21.42 mg, 0.054 mmol), Pd2(dba)3 (24.92 mg, 0.027 mmol), cesium carbonate (355 mg, 1.089 mmol) in 1,4-dioxane (2.7 mL) was heated at 120° C. for 55 mins using a microwave reactor. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was separated, washed with brine, dried and concentrated. The residue was then purified on silica eluting with a gradient of 0-100% ethyl acetate in cyclohexane to afford a material which was further purified by MDAP (acidic condition) to afford the title compound (35 mg). LCMS (A): m/z (M+H)+ 439, C21H22N6O3S requires 438 (acidic).

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe organic phase was separated
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was then purified on silica eluting with a gradient of 0-100% ethyl acetate in cyclohexane
  7. customto afford a material which
  8. customwas further purified by MDAP (acidic condition)

出典と根拠

ORDレコード
ord-e1667d3a1c4845f3a73d1b3d8a5627cb
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08877742B2

反応ノート

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