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Phosphorus oxychloride → 7-Chloro-3-phenyl-imidazo[1,2-a]pyridine-8-carbonitrile

HRID 1627014
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HRID 1627014 반응식
O[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][N:10]=[C:4]2[C:3]=1[C:17]#[N:18].O(Cl)[Cl:20].[P+5].C([O-])(O)=O.[Na+].P(Cl)(Cl)(Cl)=O>CCOCC.CCOC(C)=O>[Cl:20][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][N:10]=[C:4]2[C:3]=1[C:17]#[N:18]
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참가 물질

7

반응물 4

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178479711HCID 178479711, 화합물HCID 178510510HCID 178510510, 화합물

생성물 1

HCID 581038917-Chloro-3-phenyl-imidazo[1,2-a]pyridine-8-carbonitrile수율 33%

시약·촉매·용매 2

HCID 3283
Diethyl Ether
용매
HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

A mixture of compound D5 (2.3 g, 9.77 mmol) and phosphorus(V) oxychloride (50 ml) was heated at 120° C. for 5 h. After cooling to room temperature the solvents were evaporated in vacuo. The residue thus obtained was carefully poured into a mixture of crushed ice and NaHCO3 (aqueous sat. solution). Then EtOAc was added and the mixture was stirred for 2 h. until complete hydrolysis of the remaining phosphorus oxychloride had occurred. The organic layer was then separated, washed with brine, dried (Na2SO4) and the solvent evaporated in vacuo to give a residue that forms a precipitate upon the addition of Et2O. The solid was filtered off and dried in vacuo to yield compound D6 (0.82 g, 33%) as yellow solid.

후처리

  1. temperatureAfter cooling to room temperature the solvents
  2. customwere evaporated in vacuo
  3. customThe residue thus obtained
  4. customThe organic layer was then separated
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. customthe solvent evaporated in vacuo
  8. customto give a residue that
  9. filtrationThe solid was filtered off
  10. customdried in vacuo

출처 및 근거

ORD 기록
ord-627dd06ac0e140b3a60e6bbde86de4ab
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785486B2

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