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Sodium Carbonate → 5-[4-(4-methoxypyridin-3-yl)benzyl]-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester

HRID 1892625
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HRID 1892625 반응식
O.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1B(O)O.[C:13]([O:17][C:18]([N:20]1[CH2:29][CH2:28][C:27]2[CH:26]=[C:25]3[O:30][CH2:31][O:32][C:24]3=[CH:23][C:22]=2[CH:21]1[CH2:33][C:34]1[CH:39]=[CH:38][C:37](Br)=[CH:36][CH:35]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CC(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:13]([O:17][C:18]([N:20]1[CH2:29][CH2:28][C:27]2[CH:26]=[C:25]3[O:30][CH2:31][O:32][C:24]3=[CH:23][C:22]=2[CH:21]1[CH2:33][C:34]1[CH:35]=[CH:36][C:37]([C:5]2[CH:6]=[N:7][CH:8]=[CH:9][C:4]=2[O:3][CH3:2])=[CH:38][CH:39]=1)=[O:19])([CH3:16])([CH3:14])[CH3:15]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 441196714-Methoxypyridine-3-boronic acid monohydrateHCID 597442655-(4-Bromobenzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester

생성물 1

HCID 597442885-[4-(4-methoxypyridin-3-yl)benzyl]-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester
수율 35%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 3776Isopropanol용매

실험 절차

A mixture of 4-methoxy pyridine-3-boronic acid hydrate 19 (0.716 g, 4.684 mmol), 5-(4-bromobenzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester 38 (1.043 g, 2.342 mmol), Palladium(II) acetate (0.021 g, 0.094 mmol), triphenylphosphine (0.049 g, 0.187 mmol) and Na2CO3 (0.993 g, 9.368 mmol) in anhydrous 2-propanol (20 mL) was refluxed for 16 h. The reaction mixture was cooled to room temperature, filtered through silica, washed with ethyl acetate. The solvents were concentrated under reduced pressure. The crude residue was purified by flash column chromatography using Acetone-Hexanes (20:80 to 50:60 v/v) to yield 43 (0.389 g, 35%). MS (ES+) m/z 497 (M+Na)+.

후처리

  1. temperaturewas refluxed for 16 h
  2. filtrationfiltered through silica
  3. washwashed with ethyl acetate
  4. concentrationThe solvents were concentrated under reduced pressure
  5. customThe crude residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-2175767bd8db47b482bc8eea4a16ad38
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08507523B2

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