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Hydrochloric Acid → 2-(5-Bromo-6-(tert-butoxycarbonyl)pyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid

HRID 588691
ノート
印刷プレビュー

反応式

HRID 588691 の反応式
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([O:13]C)=[O:12])[CH2:4][CH2:3][NH:2]1.Cl.[Br:16][C:17]1[C:18]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:19][C:20](Cl)=[CH:21][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C.O>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([N:2]2[CH2:3][CH2:4][C:5]3[C:10](=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][CH:6]=3)[CH2:1]2)=[N:19][C:18]=1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]
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 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 45074001Methyl 1,2,3,4-tetrahydroisoquinoline-8-carboxylateHCID 59447676tert-Butyl 3-bromo-6-chloropyridine-2-carboxylate

生成物 1

HCID 866812722-(5-Bromo-6-(tert-butoxycarbonyl)pyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 31374Dimethylacetamide溶媒

反応条件

温度
120 °C

実験手順

A solution of methyl 1,2,3,4-tetrahydroisoquinoline-8-carboxylate, hydrochloric acid (13.6 g), tert-butyl 3-bromo-6-chloropicolinate (17.4 g) and cesium carbonate (39 g) were stirred together in N,N-dimethylacetamide (110 mL) and heated at 120° C. under nitrogen overnight. The reaction mixture was cooled, diluted with water and extracted with ethyl acetate. The organic layer was washed with brine and the combined aqueous layers were back-extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated. Silica gel chromatography using 20-100% ethyl acetate in hexanes provided the title compound.

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. extractionthe combined aqueous layers were back-extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-184a9ccc63f9497f9c50a9f96cebb4c8
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09227963B2

反応ノート

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