Dichloromethane → 3-Chloro-6-(4-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine

HRID 517802

反応式

HRID 517802 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].ClCCl.[Cl:25][C:26]1[N:30]2[N:31]=[C:32](Cl)[CH:33]=[CH:34][C:29]2=[N:28][N:27]=1>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[Cl:25][C:26]1[N:30]2[N:31]=[C:32]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:33]=[CH:34][C:29]2=[N:28][N:27]=1

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 2856454-Fluorophenylboronic acidHCID 14823463,6-Dichloro[1,2,4]triazolo[4,3-b]pyridazineHCID 17749109Barium hydroxide, octahydrate

生成物 1

HCID 446043783-Chloro-6-(4-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine収率 18.5%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

a mixture of 4.16 g of 4-fluorophenylboronic acid, 9.37 g of barium hydroxide octahydrate, 2.20 g of [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) in a complex with dichloromethane (1:1) and 5.1 g of commercial 3,6-dichloro[1,2,4]triazolo[4,3-b]pyridazine in 40 cm3 of N,N-dimethylformamide containing 10 cm3 of water is heated in a bath at 80° C. for 1.5 h. The beigey-brown suspension obtained is cooled to 20° C. and then poured into approximately 200 cm3 of water. The insoluble material is spin-filter-dried and washed successively with water and with ether, and then dried under vacuum at 20° C. The resulting beige solid is made into a paste in dichloromethane, spin-filter-dried, and dried under vacuum at 20° C. 1.24 g of 3-chloro-6-(4-fluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine are thus obtained. 30 g of silica are added to the combined mother liquors and the mixture is evaporated to dryness under vacuum. This residue is deposited onto a bed of 10 g of silica in a sintered glass filter and elution is carried out with dichloromethane. An additional 1.60 g of 3-chloro-6-(4-fluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine are thus recovered.

後処理

  1. customThe beigey-brown suspension obtained
  2. temperatureis cooled to 20° C.
  3. customThe insoluble material is spin-filter-dried
  4. washwashed successively with water and with ether
  5. customdried under vacuum at 20° C
  6. customspin-filter-dried
  7. customdried under vacuum at 20° C

出典と根拠

ORDレコード
ord-483054a9f05b47259f255761375ee790
出典データセット
uspto-grants-2015_08
特許番号
US09115134B2

関連ノート

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