Trifluoroacetic acid → 2-((6-Bromopyridin-2-yl)methyl)isoindoline-1,3-dione

HRID 17100

반응식

HRID 17100 반응식
[Br:1][C:2]1[N:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][CH:3]=1.[C:10]1(=[O:20])[NH:14][C:13](=[O:15])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(O)(C(F)(F)F)=O>O1CCCC1.O.CO>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:14]2[C:10](=[O:20])[C:11]3[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:13]2=[O:15])[CH:5]=[CH:4][CH:3]=1

참가 물질

9

반응물 5

HCID 6422Trifluoroacetic acid2회HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 3517811(6-Bromopyridin-2-yl)methanol

생성물 1

HCID 221764462-((6-Bromopyridin-2-yl)methyl)isoindoline-1,3-dione

시약·촉매·용매 3

HCID 887Methanol용매3회HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of commercially available (6-bromopyridin-2-yl)methanol (20.0 g, 0.106 mol), phthalimide (20.4 g, 0.138 mol), and triphenylphosphine (36.2 g, 0.138 mol), and 1,1′-(azodicarbonyl)-dipiperidine (34.8 g, 0.138 mol) in anhydrous tetrahydrofuran (1 L) was stirred at room temperature overnight. The precipitate was collected by vacuum filtration and washed with tetrahydrofuran. The filtrate was concentrated under reduced pressure, and the solid residue was triturated with methanol with sonication. A214.1 was collected by vacuum filtration and was dried well to give 24.1 g as a white solid. The filtrate still contained significant product which could be isolated as a second crop with methanol trituration. The compound had an HPLC retention time=2.32 min. (Column: Chromolith SpeedROD 4.6×50 mm—4 min.; Solvent A=10% MeOH, 90% H2O, and 0.1% TFA; Solvent B=90% MeOH, 10% H2O, and 0.1% TFA) and a LC/MS M+1=317.15 and 319.15.

후처리

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed with tetrahydrofuran
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe solid residue was triturated with methanol with sonication
  5. filtrationA214.1 was collected by vacuum filtration
  6. customwas dried well
  7. customto give 24.1 g as a white solid

출처 및 근거

ORD 기록
ord-b3467d2092bb4e8c87455c945af69572
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737279B2

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