Hydrochloric Acid → 6-(1,4-Diazepan-1-yl)-1-(4,4,4-trifluorobutyl)-benzo[cd]indol-2(1H)-one

HRID 433098노트

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HRID 433098 반응식
[F:1][C:2]([F:21])([F:20])[CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9]3[C:10](=[CH:16][CH:17]=[CH:18][C:8]=3[C:7]1=[O:19])[C:11](Br)=[CH:12][CH:13]=2.[NH:22]1[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.CC(C)([O-])C.[Na+].Cl>O.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].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.C1(C)C=CC=CC=1>[N:22]1([C:11]2[C:10]3[C:9]4[C:14](=[CH:13][CH:12]=2)[N:6]([CH2:5][CH2:4][CH2:3][C:2]([F:21])([F:20])[F:1])[C:7](=[O:19])[C:8]=4[CH:18]=[CH:17][CH:16]=3)[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 68163Hexahydro-1,4-diazepineHCID 187579401-(4,4,4-Trifluorobutyl)-6-bromo-benzo[cd]indol-2(1h)-oneHCID 23676156Sodium t-butoxide

생성물 1

HCID 121138336-(1,4-Diazepan-1-yl)-1-(4,4,4-trifluorobutyl)-benzo[cd]indol-2(1H)-one수율 108.5%

시약·촉매·용매 4

HCID 634876Binap, (A+-)-촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 1140Toluene용매

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온도
85 °C

실험 절차

To a mixture of 1-(4,4,4-trifluorobutyl)-6-bromo-benzo[cd]indol-2(1H)-one (1.225 g, 3.42 mmol), homopiperazine (6 g, 60 mmol) and toluene (100 ml) in a round bottomed flask was added BINAP (42 mg, 2%) and Pd2(dba)3 (30 mg, 1%) and sodium tert-butoxide (333 mg, 3.46 mmol). The reaction mixture was heated at 85° C. for 18 hours and was then poured into 500 ml concentrated HCl solution in water. The organic layer was seperated and the aqueous layer was extracted with more toluene (2×500 ml). The combined organic layers were neutralized with 10 N NaOH (aqueous ) and extracted with a one to one mixture of dichloromethane and toluene (3×500 ml). The combined organic layers were dried and filtered and concentrated to give the crude product (1.4 g).

후처리

  1. customThe organic layer was seperated
  2. extractionthe aqueous layer was extracted with more toluene (2×500 ml)
  3. extractionextracted with a one to one mixture of dichloromethane and toluene (3×500 ml)
  4. customThe combined organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-31ad57b91b62496abb888d1c79fabff2
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06667303B1

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