Water → [5-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-(4-chloro-benzyl)-amine

HRID 2261562ノート

反応式

HRID 2261562 の反応式
C(OC(=O)[N:7]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]([C:24]2[C:32]3[C:27](=[N:28][CH:29]=[C:30]([Br:33])[CH:31]=3)[NH:26][CH:25]=2)O)=[CH:18][N:17]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.O>C(#N)C>[Br:33][C:30]1[CH:31]=[C:32]2[C:24]([CH2:22][C:19]3[CH:20]=[CH:21][C:16]([NH:7][CH2:8][C:9]4[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=4)=[N:17][CH:18]=3)=[CH:25][NH:26][C:27]2=[N:28][CH:29]=1

参加物

6

反応物 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59593354(5-[(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-pyridin-2-yl)-(4-chloro-benzyl)-carbamic acid tert-butyl ester

生成物 1

HCID 59593278[5-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-(4-chloro-benzyl)-amine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To {5-[(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-pyridin-2-yl}-(4-chloro-benzyl)-carbamic acid tert-butyl ester (45, 180.0 mg, 0.33 mmol) in acetonitrile (30.0 mL) were added trifluoroacetic acid (2.0 mL, 0.026 mol) and triethylsilane (4.0 mL, 0.025 mol). The reaction was heated to reflux for 4 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified by silica gel column chromatography eluting with 10% methanol in dichloromethane to give compound (P-0038, 120 mg, 85.2%). MS (ESI)[M+H+]+=427.2, 429.2.

後処理

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 4 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with 10% methanol in dichloromethane
  9. customto give compound (P-0038, 120 mg, 85.2%)

出典と根拠

ORDレコード
ord-bc126e62187348e7a2fcf9c2769195f8
出典データセット
uspto-grants-2010_12
特許番号
US07846941B2

反応ノート

読み込み中…