Phosphorus pentachloride → 9-Benzenesulfonyl-3-bromo-5-chloro-9H-diprido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 60217ノート

反応式

HRID 60217 の反応式
[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18](O)[C:13]=3[C:12]3[CH:22]=[C:23]([Br:26])[CH:24]=[N:25][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:28]>ClC1C=CC=CC=1.ClCCl>[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18]([Cl:28])[C:13]=3[C:12]3[CH:22]=[C:23]([Br:26])[CH:24]=[N:25][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 2

HCID 24819Phosphorus pentachlorideHCID 582664728-(Benzenesulfonyl)-12-bromo-3-hydroxy-5,8,10-triazatricyclo[7.4.0.02,7]trideca-1(9),2,4,6,10,12-hexaene-4-carbonitrile

生成物 1

HCID 583651289-Benzenesulfonyl-3-bromo-5-chloro-9H-diprido[2,3-b;4',3'-d]pyrrole-6-carbonitrile収率 53%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 7964Chlorobenzene溶媒

実験手順

A solution of 9-benzenesulfonyl-3-bromo-5-hydroxy-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (2.0 g, 4.66 mmol) and phosphorus pentachloride (2.9 g, 14.0 mmol) in chlorobenzene (6 mL) was heated at 105° C. for 1 hour. The reaction mixture was cooled to ambient temperature and the solvent removed in vacuo to afford a residue. The resultant residue was dissolved in dichloromethane (300 mL) and the solution was treated with ice/water (300 mL). The layers were separated and the aqueous layer further extracted with dichloromethane (300 mL). The combined organic layer was washed with brine, dried (Na2SO4), filtered and evaporated. The resultant residue was triturated with methanol and dried to afford the title compound as a tan solid (1.1 g, 53%). 1H NMR (300 MHz, DMSO-d6): 9.70 (s, 1H), 9.06 (d, J=2.2 Hz, 1H), 8.98 (d, J=2.2 Hz, 1H), 8.27-8.22 (m, 2H), 7.77-7.76 (m, 1H), 7.67-7.60 (m, 2H).

後処理

  1. customthe solvent removed in vacuo
  2. customto afford a residue
  3. customThe layers were separated
  4. extractionthe aqueous layer further extracted with dichloromethane (300 mL)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe resultant residue was triturated with methanol
  10. customdried

出典と根拠

ORDレコード
ord-41a5125f489f4b08bc538b7c3814b433
出典データセット
uspto-grants-2016_09
特許番号
US09440976B2

反応ノート

読み込み中…