Water → HCID 57585828, 화합물

HRID 547660노트

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HRID 547660 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:5]2.O.[CH3:20][N:21](C)C=O>C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2].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-]#N.[Zn+2].[C-]#N>[C:20]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:5]2)#[N:21]

참가 물질

7

반응물 3

HCID 962WaterHCID 6228DimethylformamideHCID 57585894tert-Butyl N-(5-bromo-2,3-dihydro-1H-inden-2-yl)carbamate

생성물 1

HCID 57585828HCID 57585828, 화합물수율 78%

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 15826098Cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-yl(diphenyl)phosphane;iron(2+)촉매

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온도
110 °C

실험 절차

A flask containing 1,1-dimethylethyl (5-bromo-2,3-dihydro-1H-inden-2-yl)carbamate (3.0 g, 9.26 mmol) from the preceding step, diphenylphosphinoferrocene (645 mg, 1.16 mmol), Pd2 dba3 (532 mg, 0.58 mmol), zinc cyanide (1.50 g, 12.8 mmol) and water in 50 mL dimethylformamide was degassed four times under nitrogen and allowed to stir at 110° C. for 21 hours. Upon cooling the reaction was quenched with saturated NH4Cl and the organics were taken up in ethyl acetate. The organic layer was washed with water (3×), sat. NaCl and dried over MgSO4. The solvent was removed in vacuo and the residual orange-yellow oil was purified by silica gel column chromatography (15-40% ethyl acetate/hexanes) yielding 1.85 g (7.18 mmol, 78% yield) of the 1,1-dimethylethyl (5-cyano-2,3-dihydro-1H-inden-2-yl)carbamate as an off-white solid. 1H NMR (400 MHz, CDCl3) delta 7.47 (s, 1H), 7.45 (d, 1H, J=7.9 Hz), 7.28 (d, 1H, J=7.7 Hz), 4.69 (br.s), 1H), 4.47 (s(br), 1H), 3.33-3.25 (m, 2H), 2.86-2.80 (m, 2H), 2.79 (s, 9H) ppm. (M+1) 259.1, 2.46 min (LC/MS method A).

후처리

  1. customwas degassed four times under nitrogen
  2. temperatureUpon cooling the reaction
  3. customwas quenched with saturated NH4Cl
  4. washThe organic layer was washed with water (3×), sat. NaCl
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo
  7. customthe residual orange-yellow oil was purified by silica gel column chromatography (15-40% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-4054291e337f4baba72c0123be33ba33
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939528B2

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