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

HRID 60217노트

반응식

HRID 60217 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 7964Chlorobenzene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-41a5125f489f4b08bc538b7c3814b433
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440976B2

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