Trimethyl-(6-methylpyrazin-2-yl)stannane → tert-butyl N-[(3S)-1-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-2-oxo-3-piperidyl]carbamate

HRID 57933ノート

反応式

HRID 57933 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[N:16]=[C:15]([N:17]4[CH2:22][CH2:21][CH2:20][C@H:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:18]4=[O:31])[CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.C[Sn](C)(C)[C:34]1[CH:39]=[N:38][CH:37]=[C:36]([CH3:40])[N:35]=1>CN(C)C(=O)C>[CH3:40][C:36]1[N:35]=[C:34]([C:2]2[N:7]=[CH:6][C:5]3[CH:8]=[N:9][N:10]([C:11]4[N:16]=[C:15]([N:17]5[CH2:22][CH2:21][CH2:20][C@H:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:27])[CH3:28])[C:18]5=[O:31])[CH:14]=[CH:13][CH:12]=4)[C:4]=3[CH:3]=2)[CH:39]=[N:38][CH:37]=1

参加物

4

反応物 2

HCID 86707041Trimethyl-(6-methylpyrazin-2-yl)stannaneHCID 86707118tert-butyl N-[(3S)-1-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]-2-oxo-3-piperidyl]carbamate

生成物 1

HCID 86707119tert-butyl N-[(3S)-1-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-2-oxo-3-piperidyl]carbamate

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
145 °C

実験手順

A solution of tert-butyl N-[(3S)-1-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]-2-oxo-3-piperidyl]carbamate (125 mg, 0.282 mmol) and palladium(0)tetrakis(triphenylphosphine) (32 mg, 0.028 mmol) in N,N-dimethylacetamide 5.0 mL was added trimethyl-(6-methylpyrazin-2-yl)stannane (145 mg, 0.565 mmol). The reaction mixture heated at 145° C. for 40 min in CEM microwave. The reaction mixture was filtered through celite and concentrated. The crude product was diluted with EtOAc then washed with water. The organic layers was dried with sodium sulfate, filtered, and concentrated in vacuum. The crude product was carried to next step. MS (ESI) m/z: 501.1.

後処理

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated
  3. additionThe crude product was diluted with EtOAc
  4. washthen washed with water
  5. dry with materialThe organic layers was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum

出典と根拠

ORDレコード
ord-acdb07c56cad45f7b3de64efa2089dd7
出典データセット
uspto-grants-2016_09
特許番号
US09434725B2

反応ノート

読み込み中…