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

HRID 1193380ノート

反応式

HRID 1193380 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-5b6425934f3247b6b2b718021c870543
出典データセット
uspto-grants-2014_03
特許番号
US08680159B2

反応ノート

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