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Potassium Carbonate → 9-tert-butyl-3-methoxy-2-pyridin-3-yl-14-(1,3-thiazol-5-yl)-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-one

HRID 1971693
ノート
印刷プレビュー

反応式

HRID 1971693 の反応式
Br[C:2]1[C:3]([O:31][CH3:32])=[CH:4][C:5]2[CH2:6][CH2:7][N:8]3[C:14]4[C:15](=[O:25])[N:16]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:17][CH2:18]O[CH2:20][C:13]=4[C:12]([C:26]4[S:30][CH:29]=[N:28][CH:27]=4)=[C:9]3[C:10]=2[CH:11]=1.B(O)(O)[C:34]1[CH:39]=[CH:38][CH:37]=[N:36][CH:35]=1.[C:42]([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(COC)OC>[C:21]([N:16]1[CH2:17][CH2:18][CH2:42][CH2:20][C:13]2[C:12]([C:26]3[S:30][CH:29]=[N:28][CH:27]=3)=[C:9]3[C:10]4[CH:11]=[C:2]([C:34]5[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=5)[C:3]([O:31][CH3:32])=[CH:4][C:5]=4[CH2:6][CH2:7][N:8]3[C:14]=2[C:15]1=[O:25])([CH3:23])([CH3:22])[CH3:24]
参加物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 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 27343783-Pyridinylboronic acidHCID 581248172-bromo-9-tert-butyl-3-methoxy-14-(1,3-thiazol-5-yl)-5,6,10,11-tetrahydro-9H-[1,4]oxazocino[7',6':4,5]pyrrolo[2,1-a]isoquinolin-8(13H)-one

生成物 1

HCID 509063619-tert-butyl-3-methoxy-2-pyridin-3-yl-14-(1,3-thiazol-5-yl)-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-one
収率 88.1%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A degassed solution of 40 mg of 11i, 20 mg of pyridyl-3-boronic acid, 30 mg of K2CO3, 12 mg Pd(PPh3)4 and 3 ml of 90% aq. dimethoxyethane was heated at 90° C. for 16 hr. The reaction mixture was cooled, poured into 20 ml of 1N NaOH and extracted with ethyl acetate. The organic layer was washed with water, dried, concentrated and the residues were passed through a short silica column, using a gradient of toluene/acetone as eluent. The isolated material was treated with diethyl ether and gave 35 mg of 11j as white crystals; Mp: 227-229° C.; Rf 0.35 (toluene/acetone 1/1).

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. additionThe isolated material was treated with diethyl ether

出典と根拠

ORDレコード
ord-ae424c688ee146afb987c10b99e7650b
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08431564B2

反応ノート

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