2,2,2-Cryptand → (+/-)-2-tert-butyl-4-chloro 5-(4-(1-fluoro-but-2-oxy)benzyl)oxy-3(2H)-pyridazinone

HRID 1516048ノート

反応式

HRID 1516048 の反応式
[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:22]([CH2:35][CH3:36])[CH2:23]OS(C3C=CC(C)=CC=3)(=O)=O)=[CH:17][CH:16]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[F-:37].[K+].C1N2CCOCCOCCN(CCOCCOCC2)CCOCCOC1>C(#N)C>[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:22]([CH2:35][CH3:36])[CH2:23][F:37])=[CH:17][CH:16]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 728012,2,2-CryptandHCID 522689Potassium FluorideHCID 59678622(+/-)-2-tert-butyl 4-chloro 5-(4-(1-tosyloxy-but-2-oxy) benzyl)oxy 3(2H)-pyridazinone

生成物 1

HCID 44576650(+/-)-2-tert-butyl-4-chloro 5-(4-(1-fluoro-but-2-oxy)benzyl)oxy-3(2H)-pyridazinone収率 65%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

The product of Example 3F (28 mg, 52.4 μmol) was dissolved in 0.5 mL acetonitrile in a 5 mL flask and to this was added a solution of potassium fluoride (4.5 mg, 78.6 μmol) and Kryptofix 222 (29.6 mg, 78.6 μmol) in 0.5 mL acetonitrile. The above solution was then immersed in a oil bath preheated to 90° C. The reaction was allowed to stir for 90 minutes after which all the volatiles were removed under reduced pressure and the crude mixture purified by preparative thin layer chromatography to obtain 13 mg (65%) of pure desired compound. 1H (CDCl3) δ (ppm): 7.72 (s, 1H), 7.3 (d, 2H), 6.9 (d, 2H), 5.23 (s, 2H), 4.57-4.59 (m, 2H), 4.4 (m, 4H), 1.74 (m, 2H), 1.6 (s, 9H), 1.0 (t, 3H). 13C (CDCl3) δ (ppm): 159, 158.7, 153.7, 129, 127.5, 125.2, 118.3, 116.4, 83.85 (d, 1JCF=172.2), 78, 71.1, 66.3, 27.8, 23.2, 9.48. 19F (CDCl3, CFCl3 as internal standard) δ (ppm): −228 (d of t, J=−19, −60 Hz)

後処理

  1. customThe above solution was then immersed in a oil bath
  2. custompreheated to 90° C
  3. customwere removed under reduced pressure
  4. customthe crude mixture purified by preparative thin layer chromatography

出典と根拠

ORDレコード
ord-6077da71273b489a8fcb10337922a221
出典データセット
uspto-grants-2012_07
特許番号
US08226929B2

反応ノート

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