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Potassium Carbonate → [3-Acetyl-6-(4-methoxy-benzylamino)-pyrrolo[2,3-b]pyridin-1-yl]-acetic acid tert-butyl ester

HRID 1527261
ノート
印刷プレビュー

反応式

HRID 1527261 の反応式
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH3:10][O:11][C:12]1[CH:31]=[CH:30][C:15]([CH2:16][NH:17][C:18]2[N:23]=[C:22]3[NH:24][CH:25]=[C:26]([C:27](=[O:29])[CH3:28])[C:21]3=[CH:20][CH:19]=2)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC#N.C1COCC1>[C:6]([O:5][C:3](=[O:4])[CH2:2][N:24]1[C:22]2=[N:23][C:18]([NH:17][CH2:16][C:15]3[CH:14]=[CH:13][C:12]([O:11][CH3:10])=[CH:31][CH:30]=3)=[CH:19][CH:20]=[C:21]2[C:26]([C:27](=[O:29])[CH3:28])=[CH:25]1)([CH3:9])([CH3:8])[CH3:7]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium Carbonate2 回HCID 79177tert-Butyl bromoacetate2 回HCID 682841881-[6-(4-Methoxy-benzylamino)-1H-pyrrolo[2,3-b]pyridin-3-yl]-ethanone

生成物 1

HCID 68283638[3-Acetyl-6-(4-methoxy-benzylamino)-pyrrolo[2,3-b]pyridin-1-yl]-acetic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

Tert-butyl bromoacetate (27 μL, 0.18 mmol) was added to a suspension of 1-[6-(4-methoxy-benzylamino)-1H-pyrrolo[2,3-b]pyridin-3-yl]-ethanone (0.17 mmol) and potassium carbonate (27.5 mg, 0.20 mmol) in CH3CN (0.33 mL) and THF (0.33 mL). The reaction mixture was stirred at RT for 7 h. Potassium carbonate (27.5 mg, 0.20 mmol) and tert-butyl bromoacetate (27 μL, 0.18 mmol) were added again and stirring was continued overnight, this operation was repeated the next day. The suspension was filtered, the filtrate concentrated under reduced pressure and the crude residue was purified by flash column chromatography on silica gel (CH2Cl2 to CH2Cl2/MeOH 98:2). TLC, Rf (CH2Cl2/MeOH 9:1)=0.9; MS (UPLC/MS): 410.2 [M+H]+, 819.4 [2M+H]+, 841.3 [2M+Na]+, 454.1 [M+HCOO]−; tR (HPLC conditions f): 2.30 min.

後処理

  1. stirringstirring
  2. waitwas continued overnight
  3. filtrationThe suspension was filtered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customthe crude residue was purified by flash column chromatography on silica gel (CH2Cl2 to CH2Cl2/MeOH 98:2)
  6. custom2.30 min.

出典と根拠

ORDレコード
ord-82a0d3638cd741bcafdb3cdb2f2dae95
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09085555B2

反応ノート

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