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6-Bromoisoquinoline → tert-Butyl 8-(isoquinolin-6-yl)-2,8-diazaspiro[4.5]decane-2-carboxylate

HRID 1253703
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HRID 1253703 반응식
[CH2:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][N:2]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].Br[C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[N:24][CH:23]=[CH:22]2.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.[Pd].C([O-])(=O)C>[CH:25]1[C:26]2[C:21](=[CH:20][C:19]([N:8]3[CH2:7][CH2:6][C:5]4([CH2:1][N:2]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3][CH2:4]4)[CH2:10][CH2:9]3)=[CH:28][CH:27]=2)[CH:22]=[CH:23][N:24]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 3136816-BromoisoquinolineHCID 634876Binap, (A+-)-HCID 34178604tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate

생성물 1

HCID 66700964tert-Butyl 8-(isoquinolin-6-yl)-2,8-diazaspiro[4.5]decane-2-carboxylate수율 52%

시약·촉매·용매 2

HCID 9793925palladium(I)acetate촉매
HCID 1140
Toluene
용매

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온도
120 °C

실험 절차

Sodium t-butylate (6.24 mmol, 3.0 eq.) was added to a solution of tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (2.08 mmol, 1.0 eq.) and 6-bromoisoquinoline (2.08 mmol, 1.0 eq.) in toluene (10 ml) and the reaction mixture was degassed with N2. BINAP (0.124 mmol, 0.06 eq.) and Pd acetate (0.04 mmol, 0.02 eq.) were added and the mixture was heated at 120° C. for 12 h. The reaction mixture was filtered over Celite and the filtrate was concentrated on a rotary evaporator. The crude product was purified by means of column chromatography (silica gel, 5% methanol in methylene chloride) in order to obtain the desired product. Yield: 52%

후처리

  1. customthe reaction mixture was degassed with N2
  2. filtrationThe reaction mixture was filtered over Celite
  3. concentrationthe filtrate was concentrated on a rotary evaporator
  4. customThe crude product was purified by means of column chromatography (silica gel, 5% methanol in methylene chloride) in order

출처 및 근거

ORD 기록
ord-3bf872bff1f7480ea9de142df912f99b
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08455475B2

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