Cesium carbonate → HCID 131734957、化合物

HRID 921947ノート

反応式

HRID 921947 の反応式
Br[C:2]1[C:3]([Cl:18])=[C:4]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.[CH2:19]1[C:23]2([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:22][CH2:21][N:20]1[C:29](=[O:31])[CH3:30].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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]>[C:29]([N:20]1[CH2:21][CH2:22][C:23]2([CH2:28][CH2:27][N:26]([C:2]3[C:3]([Cl:18])=[C:4]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=3)[CH2:25][CH2:24]2)[CH2:19]1)(=[O:31])[CH3:30]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 21060031HCID 21060031、化合物HCID 86708481Tert-butyl (3-bromo-2-chloro-5-cyanophenyl)carbamate

生成物 1

HCID 131734957HCID 131734957、化合物収率 50.5%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
105 °C

実験手順

A mixture of tert-butyl (3-bromo-2-chloro-5-cyanophenyl)carbamate (291 mg, 0.878 mmol), 1-(2,8-diazaspiro[4.5]decan-2-yl)ethanone (160 mg, 0.878 mmol), Pd2dba3 (80 mg, 0.088 mmol), BINAP (164 mg, 0.263 mmol), and Cs2CO3 (858 mg, 2.63 mmol) in Dioxane (15 mL) was evacuated and filled with nitrogen 3× and heated at 105° C. overnight. The reaction mixture was filtered through a plug of celite and the filtrate was concentrated. The crude product was purified by flash chromatography on silica gel using an automated ISCO system (40 g column, eluting with 10% to 100% EtOAc in Hexane) gave tert-butyl (3-(2-acetyl-2,8-diazaspiro[4.5]decan-8-yl)-2-chloro-5-cyanophenyl)carbamate (192 mg)

後処理

  1. customwas evacuated
  2. additionfilled with nitrogen 3×
  3. filtrationThe reaction mixture was filtered through a plug of celite
  4. concentrationthe filtrate was concentrated
  5. customThe crude product was purified by flash chromatography on silica gel using
  6. washan automated ISCO system (40 g column, eluting with 10% to 100% EtOAc in Hexane)

出典と根拠

ORDレコード
ord-cf34651fa56b43b687960f480743c8d8
出典データセット
uspto-grants-2016_03
特許番号
US09273057B2

反応ノート

読み込み中…