Potassium Carbonate → 2-(6-Chlorohex-1-ynyl)pyridin-3-amine

HRID 573281ノート

反応式

HRID 573281 の反応式
Cl[C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].C1C=CC(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:45][CH2:46][CH2:47][CH2:48][CH2:49][C:50]#[CH:51]>CC([O-])=O.CC([O-])=O.[Pd+2].CC#N>[Cl:45][CH2:46][CH2:47][CH2:48][CH2:49][C:50]#[C:51][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 805282-Chloro-3-pyridylamineHCID 821241,4-Bis(diphenylphosphino)butaneHCID 2720016-Chloro-1-hexyne

生成物 1

HCID 667276242-(6-Chlorohex-1-ynyl)pyridin-3-amine収率 14.4%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒

実験手順

A mixture of 2-chloropyridin-3-amine (2571 mg), K2CO3 (8292 mg), Pd(OAc)2 (180 mg), dppb (682 mg) and CH3CN (25 mL) was stirred at room temperature under Ar atmosphere for 30 min. 6-Chlorohex-1-yne (2565 mg) was added to the mixture, and the mixture was stirred at 80° C. under Ar atmosphere for 24 h. The mixture was filtrated and insoluble material was washed with CH3CN. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (600 mg).

後処理

  1. stirringthe mixture was stirred at 80° C. under Ar atmosphere for 24 h
  2. filtrationThe mixture was filtrated
  3. washinsoluble material was washed with CH3CN
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (AcOEt/hexane)

出典と根拠

ORDレコード
ord-671f0a580971406aae01033702553235
出典データセット
uspto-grants-2015_05
特許番号
US09029536B2

反応ノート

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