5-bromo-N,N-dimethylpyridin-2-amine → Benzyl 1-(6-(dimethylamino)pyridin-3-yl)piperidin-4-yl(methyl)carbamate

HRID 1193380노트

반응식

HRID 1193380 반응식
[CH3:1][N:2]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[C:3](=[O:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Br[C:20]1[CH:21]=[CH:22][C:23]([N:26]([CH3:28])[CH3:27])=[N:24][CH:25]=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:27][N:26]([CH3:28])[C:23]1[N:24]=[CH:25][C:20]([N:16]2[CH2:15][CH2:14][CH:13]([N:2]([CH3:1])[C:3](=[O:12])[O:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:18][CH2:17]2)=[CH:21][CH:22]=1

참가 물질

5

반응물 2

HCID 38030415-bromo-N,N-dimethylpyridin-2-amineHCID 18677746Benzyl methyl(piperidin-4-yl)carbamate

생성물 1

HCID 66799303Benzyl 1-(6-(dimethylamino)pyridin-3-yl)piperidin-4-yl(methyl)carbamate수율 67%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

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온도
80 °C

실험 절차

Benzyl methyl(piperidin-4-yl)carbamate (stage 3 AMN-52) (616 mg, 2.4875 mmol, 1.0 eq.), 5-bromo-2-dimethylaminopyridine (500 mg, 2.4875 mmol, 1.0 eq.) and KOBut (557 mg, 4.978 mmol, 2.0 eq.) were taken up in toluene (15 ml) and degassed with N2. BI NAP (77 mg, 0.124 mmol, 0.05 eq.) and Pd2(dba)3 (113 mg, 0.124 mmol, 0.05 eq.) were then added and the mixture was heated for 16 hours at 80° C. After monitoring by TLC, the reaction mixture was filtered over Celite and the filtrate was concentrated under reduced pressure and purified by column chromatography (silica gel, 2% MeOH in DCM). Yield: 67% (500 mg, 1.358 mmol)

후처리

  1. customdegassed with N2
  2. filtrationthe reaction mixture was filtered over Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. custompurified by column chromatography (silica gel, 2% MeOH in DCM)

출처 및 근거

ORD 기록
ord-5b6425934f3247b6b2b718021c870543
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680159B2

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