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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
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HRID 1971693 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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

생성물 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
수율 88.1%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ae424c688ee146afb987c10b99e7650b
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08431564B2

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