Dichloromethane → (+/-)-2-(Hydroxymethyl)-6,8-dihydrospiro[cyclopenta[g]quinoxaline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 551102노트

반응식

HRID 551102 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][C:19]=1[N+:20]([O-])=O)[CH2:16][C@:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]1=[O:15])[CH2:5]2.[O-]S([O-])(=O)=O.[Mg+2].[CH2:29]([O-:31])[CH3:30].[CH2:32](Cl)Cl>CO>[OH:31][CH2:29][C:30]1[CH:32]=[N:1][C:2]2[CH:3]=[C:4]3[CH2:5][C:6]4([C:14]5[C:9](=[N:10][CH:11]=[CH:12][CH:13]=5)[NH:8][C:7]4=[O:15])[CH2:16][C:17]3=[CH:18][C:19]=2[N:20]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 1194401-Hydroxyethyl radical2회HCID 67174155(S)-5-Amino-6-nitro-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one2회

생성물 1

HCID 67173211(+/-)-2-(Hydroxymethyl)-6,8-dihydrospiro[cyclopenta[g]quinoxaline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of 5,6-diamino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (320 mg, 1.20 mmol, described in Intermediate 13) and MgSO4 (1.06 g, 8.81 mmol) in CH2Cl2 (15 mL) and CH3OH (15 mL) was added the ethanolate of hydroxypyruvic aldehyde trimer [Evans et al., J. Am. Chem. Soc. 1938, 60, 1628-1629] (320 mg, 1.0 mmol). After 4 h, more of the ethanolate of hydroxypyruvic aldehyde trimer (340 mg, 1.1 mmol) was added and the mixture was heated to reflux for 2 h. The reaction mixture was partitioned between brine (50 mL) and EtOAc (150 mL). The organic layer was removed and the aqueous layer was extracted further with EtOAc (2×100 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 90:10, to give the title compound. MS: m/z=319 (M+1).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h
  3. customThe reaction mixture was partitioned between brine (50 mL) and EtOAc (150 mL)
  4. customThe organic layer was removed
  5. extractionthe aqueous layer was extracted further with EtOAc (2×100 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by silica gel chromatography
  10. washeluting with a gradient of CH2Cl2

출처 및 근거

ORD 기록
ord-cda2bd18f09a4bf5adebc046295b1016
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947677B2

반응 노트

불러오는 중…