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

HRID 433098ノート

反応式

HRID 433098 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 634876Binap, (A+-)-触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
85 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-31ad57b91b62496abb888d1c79fabff2
出典データセット
uspto-grants-2003_12
特許番号
US06667303B1

反応ノート

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