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

HRID 331062
ノート
印刷プレビュー

反応式

HRID 331062 の反応式
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:22])[C:9]([CH3:21])=[C:10]([C:11]3[CH:19]=[C:18]4[C:14]([CH2:15][CH2:16][N:17]4[CH3:20])=[CH:13][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.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.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]>[CH3:22][N:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([NH:32][S:29]([C:26]3[CH:27]=[CH:28][N:24]([CH3:23])[N:25]=3)(=[O:31])=[O:30])=[C:3]2[C:10]([C:11]2[CH:19]=[C:18]3[C:14]([CH2:15][CH2:16][N:17]3[CH3:20])=[CH:13][CH:12]=2)=[C:9]1[CH3:21]
参加物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 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 148356431-methyl-1H-pyrazole-3-sulfonamideHCID 710901424-bromo-1,2-dimethyl-3-(1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 71090219N-(1,2-dimethyl-3-(1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-1-methyl-1H-pyrazole-3-sulfonamide
収率 32.4%

試薬・触媒・溶媒 2

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

実験手順

A mixture of 4-bromo-1,2-dimethyl-3-(1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridine (D28) (390 mg, 1.095 mmol), 1-methyl-1H-pyrazole-3-sulfonamide (D94) (265 mg, 1.642 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (95 mg, 0.164 mmol), cesium carbonate (1070 mg, 3.28 mmol) and Pd2(dba)3 (75 mg, 0.082 mmol) in 1,4-dioxane (10 mL) was refluxed for 7 hours. After cooled to RT, the reaction mixture was filtered through celite, washing with DCM and the resulting solution was evaporated to dryness. DCM was added to the residue and the resulting solid was filtered and then taken up in formic acid/DMSO (1:1), purified by MDAP (acidic condition) to give the title compound (155 mg). LCMS (A): m/z (M+H)+ 437, C22H24N6O2S requires 436 (acidic).

後処理

  1. temperaturewas refluxed for 7 hours
  2. filtrationthe reaction mixture was filtered through celite
  3. washwashing with DCM
  4. customthe resulting solution was evaporated to dryness
  5. additionDCM was added to the residue
  6. filtrationthe resulting solid was filtered
  7. custompurified by MDAP (acidic condition)

出典と根拠

ORDレコード
ord-c5c02f3ca8a145d5b77f79e12ed09d71
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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