Cesium carbonate → HCID 131734957, 화합물

HRID 921947노트

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HRID 921947 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 131734957HCID 131734957, 화합물수율 50.5%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
105 °C

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-cf34651fa56b43b687960f480743c8d8
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273057B2

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