Trifluoroacetic acid → [5-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-(6-methoxy-pyridin-3-ylmethyl)-amine

HRID 510003ノート

反応式

HRID 510003 の反応式
C(OC(=O)[N:7]([C:17]1[CH:22]=[CH:21][C:20]([CH:23]([C:26]2[C:34]3[C:29](=[N:30][CH:31]=[C:32]([Br:35])[CH:33]=3)[NH:28][CH:27]=2)OC)=[CH:19][N:18]=1)[CH2:8][C:9]1[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[Br:35][C:32]1[CH:33]=[C:34]2[C:26]([CH2:23][C:20]3[CH:21]=[CH:22][C:17]([NH:7][CH2:8][C:9]4[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=4)=[N:18][CH:19]=3)=[CH:27][NH:28][C:29]2=[N:30][CH:31]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58259147{5-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methoxy-methyl]-pyridin-2-yl}-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester

生成物 1

HCID 67200583[5-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-(6-methoxy-pyridin-3-ylmethyl)-amine収率 61.8%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

To {5-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methoxy-methyl]-pyridin-2-yl}-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (154, 0.35 g, 0.63 mmol) in 20.0 mL of acetonitrile, triethylsilane (1.0 mL, 6.3 mmol) and trifluoroacetic acid (0.50 mL, 6.5 mmol) were added and the reaction stirred at 80° C. for 4 hours. The reaction was concentrated under vacuum and combined with aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 20-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (P-2017, 165.1 mg). MS (ESI) [M+H+]+=423.8, 425.8

後処理

  1. concentrationThe reaction was concentrated under vacuum
  2. extractionextracted with ethyl acetate
  3. filtrationThe organic layer was filtered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material was purified by silica gel column chromatography
  6. washeluting with 20-100% ethyl acetate in hexane
  7. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-0eb8d695fe8341f799b1e602275e9e08
出典データセット
uspto-grants-2015_08
特許番号
US09096593B2

反応ノート

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