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Dimethylformamide → 5-{3-[2,6-difluoro-3-(propane-1-sulfonylamino)-benzoyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-pyridine-2-carboxylic acid ethylamide

HRID 217622
ノート
印刷プレビュー

反応式

HRID 217622 の反応式
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:20]([CH:21]([C:23]4[C:28]([F:29])=[CH:27][CH:26]=[C:25]([NH:30][S:31]([CH2:34][CH2:35][CH3:36])(=[O:33])=[O:32])[C:24]=4[F:37])[OH:22])=[CH:19][NH:18][C:15]3=[N:16][CH:17]=2)=[CH:8][N:7]=1)=[O:5])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CN(C)C=O>O1CCCC1>[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:20]([C:21](=[O:22])[C:23]4[C:28]([F:29])=[CH:27][CH:26]=[C:25]([NH:30][S:31]([CH2:34][CH2:35][CH3:36])(=[O:33])=[O:32])[C:24]=4[F:37])=[CH:19][NH:18][C:15]3=[N:16][CH:17]=2)=[CH:8][N:7]=1)=[O:5])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 159087TriacetoxyperiodinaneHCID 595696145-(3-{[2,6-difluoro-3-(propane-1-sulfonylamino)-phenyl]-hydroxy-methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-pyridine-2-carboxylic acid ethylamide

生成物 1

HCID 497793825-{3-[2,6-difluoro-3-(propane-1-sulfonylamino)-benzoyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-pyridine-2-carboxylic acid ethylamide収率 61.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 5-(3-{[2,6-difluoro-3-(propane-1-sulfonylamino)-phenyl]-hydroxy-methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-pyridine-2-carboxylic acid ethylamide (73, 50 mg, 0.094 mmol) dissolved in 0.76 mL of tetrahydrofuran, Dess-Martin periodinane (48 mg, 0.113 mmol) was added, followed by 1 mL of dimethylformamide. The reaction was allowed to stir at room temperature for 1 hour, then quenched with water and the aqueous layer extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting residue was purified by silica gel column chromatography to provide the desired compound (P-2151, 30.6 mg). MS (ESI) [M+H+]+=528.2.

後処理

  1. customquenched with water
  2. extractionthe aqueous layer extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe resulting residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-a1f6fbe4d4984609bfc5165c30f0a787
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08198273B2

反応ノート

読み込み中…

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