Benzyl methyl(piperidin-4-yl)carbamate → HCID 66798915、化合物

HRID 1193374ノート

反応式

HRID 1193374 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:25]=[CH:24][N:23]=[C:22]([N:26]([CH3:28])[CH3:27])[CH:21]=1.C(O[Na])(C)(C)C>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:22]1[CH:21]=[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:25]=[CH:24][N:23]=1

参加物

6

反応物 3

HCID 18677746Benzyl methyl(piperidin-4-yl)carbamateHCID 234369354-Bromo-N,N-dimethylpyridin-2-amineHCID 178418730sodium 2-methylpropan-2-olate

生成物 1

HCID 66798915HCID 66798915、化合物収率 63%

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 (0.862 mmol, 1.0 eq.), 4-bromo-N,N-dimethylpyridin-2-amine (173 mg, 0.862 mmol, 1.0 eq.) and t-BuONa (193 mg, 1.72 mmol, 2.0 eq.) were taken up in toluene (10 ml) and degassed with N2. BI NAP (26 mg, 0.043 mmol, 0.05 eq.) and Pd2(dba)3 (39 mg, 0.043 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, 4% MeOH in DCM). Yield: 63% (200 mg, 03543 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, 4% MeOH in DCM)

出典と根拠

ORDレコード
ord-58f8839a0e654266bef0d0c725e3e777
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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