Nitrogen → 9-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 886058노트

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HRID 886058 반응식
[Br:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]3[N:10]([CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1)[CH:9]=[C:8](I)[N:7]=3.N#N.C[Si](C)(C)N[Si](C)(C)C.C[N:29](C)[CH:30]=[O:31]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]3[N:10]([CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1)[CH:9]=[C:8]([C:30]([NH2:29])=[O:31])[N:7]=3

참가 물질

6

반응물 4

HCID 947NitrogenHCID 6228DimethylformamideHCID 13838HexamethyldisilazaneHCID 582048589-Bromo-2-iodo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine

생성물 1

HCID 582046299-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide수율 76%

시약·촉매·용매 1

HCID 178418476HCID 178418476, 화합물촉매

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온도
70 °C

실험 절차

Alternatively, a solution of 8-Bromo-2-iodo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene (10.00 g, 0.02558 mol) in N,N-Dimethylformamide (250 mL) was thoroughly degassed with N2. Bis(triphenylphosphine)palladium(II) chloride (0.807 g, 0.00115 mol) was added followed by Hexamethyldisilazane (21.58 mL, 0.1023 mol). The solution was flushed with CO for 2 minutes and then sealed with a CO balloon attached. The reaction was heated to 70° C. for 2.5 hours. Methylene chloride and saturated NH4Cl were added and the mixture was extracted 4 times with methylene chloride. The organic phases were combined, dried with MgSO4 and concentrated. A small amount of isopropanol was added and the mixture was triturated overnight. The mixture was filtered to yield 5.97 g (76% yield) of 8-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid amide as a fine brown powder. MS (ESI+) 308.0/310.0

후처리

  1. customThe solution was flushed with CO for 2 minutes
  2. customsealed with a CO balloon
  3. additionMethylene chloride and saturated NH4Cl were added
  4. extractionthe mixture was extracted 4 times with methylene chloride
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. additionA small amount of isopropanol was added
  8. customthe mixture was triturated overnight
  9. filtrationThe mixture was filtered

출처 및 근거

ORD 기록
ord-fb103d4f0c81454d8bd0db6df0c9888f
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242104B2

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