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Dimethylformamide → 2(5-cyanopyridin-2-yl)-N-(4-{[1-(propan-2-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl]carbonyl}pyridin-2-yl)acetamide

HRID 1753003
ノート
印刷プレビュー

反応式

HRID 1753003 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[C:16]([C:18]([C:20]3[C:24]4[CH:25]=[N:26][CH:27]=[CH:28][C:23]=4[N:22]([CH:29]([CH3:31])[CH3:30])[CH:21]=3)=[O:19])[CH:15]=[CH:14][N:13]=2)=[O:10])=[N:6][CH:7]=1.[CH3:32][N:33](C=O)C>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.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].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:32]([C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[C:16]([C:18]([C:20]3[C:24]4[CH:25]=[N:26][CH:27]=[CH:28][C:23]=4[N:22]([CH:29]([CH3:31])[CH3:30])[CH:21]=3)=[O:19])[CH:15]=[CH:14][N:13]=2)=[O:10])=[N:6][CH:7]=1)#[N:33]
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 2

HCID 6228DimethylformamideHCID 900941972-(5-bromopyridin-2-yl)-N-(4-{[1-(propan-2-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl]carbonyl}pyridin-2-yl)acetamide

生成物 1

HCID 1183412202(5-cyanopyridin-2-yl)-N-(4-{[1-(propan-2-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl]carbonyl}pyridin-2-yl)acetamide

試薬・触媒・溶媒 4

HCID 11186Zinc cyanide (Zn(CN)2)触媒
HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
触媒
HCID 9811564Bis(dibenzylideneacetone)palladium触媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-(5-bromopyridin-2-yl)-N-(4-{[1-(propan-2-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl]carbonyl}pyridin-2-yl)acetamide (Example 237, 40 mg, 0.083 mmol), zinc cyanide (29 mg, 0.251 mmol), Pd2(dba)3 (3 mg, 0.003 mmol) and DPPF (7.5 mg, 0.013 mmol) in DMF (1 mL) was heated to 100° C. under microwave irradiation for 25 minutes. The reaction was cooled and diluted with ethyl acetate. The organic layer was collected, washed with water, brine, dried over sodium sulphate and concentrated in vacuo. The residue was purified using preparative TLC eluting with 5% MeOH in DCM to afford the LCMS (5 minute run) Rt=2.78 minutes MS m/z 425 [M+H]+

後処理

  1. temperatureThe reaction was cooled
  2. customThe organic layer was collected
  3. washwashed with water, brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified
  7. washeluting with 5% MeOH in DCM
  8. customto afford the LCMS (5 minute run) Rt=2.78 minutes MS m/z 425

出典と根拠

ORDレコード
ord-f3e8403907884c2280ecf84d8503ea8d
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09163021B2

反応ノート

読み込み中…

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