Triphenylphosphine → Triphenylphosphine Oxide

HRID 538344노트

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HRID 538344 반응식
[N:1]([CH2:4][C:5]([O:15]S(C)(=O)=O)([C:7]1[C:12]([F:13])=[CH:11][N:10]=[C:9]([Br:14])[CH:8]=1)[CH3:6])=[N+]=[N-].[CH:20]1[CH:25]=[CH:24][C:23]([P:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:22][CH:21]=1>C1COCC1>[Br:14][C:9]1[CH:8]=[C:7]([C:5]2([CH3:6])[CH2:4][NH:1]2)[C:12]([F:13])=[CH:11][N:10]=1.[P:26]([C:23]1[CH:22]=[CH:21][CH:20]=[CH:25][CH:24]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:15]

참가 물질

5

반응물 2

HCID 11776TriphenylphosphineHCID 86668053Methanesulfonic acid 2-azido-1-(2-bromo-5-fluoro-pyridin-4-yl)-1-methyl-ethyl ester

생성물 2

HCID 13097Triphenylphosphine OxideHCID 866680542-Bromo-5-fluoro-4-(2-methyl-aziridin-2-yl)-pyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of methanesulfonic acid 2-azido-1-(2-bromo-5-fluoro-pyridin-4-yl)-1-methyl-ethyl ester (2.1 g, 6.09 mmol) and PPh3 (1.597 g, 6.09 mmol) in THF (20 mL) was stirred at rt for 30 min. The reaction mixture was evaporated to dryness, the residue was taken up with TBME and 10% aq. citric acid soln. The aq. phase was reextracted with TBME, the combined org. phases were washed with H2O. The combined aq. phases were basified using 2N aq. NaOH soln. and three times extracted with TBME. The combined org. phases were dried over Na2SO4, filtered and concentrated to yield 2-bromo-5-fluoro-4-(2-methyl-aziridin-2-yl)-pyridine in a mixture with Ph3PO that was used for the next step without further purification, HPLC RtH4=0.96 min; ESIMS: 231, 233 [(M+H)+].

후처리

  1. customThe reaction mixture was evaporated to dryness
  2. washphases were washed with H2O
  3. extractionand three times extracted with TBME
  4. dry with materialphases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ce7f7842e1ea4eb9873c05b84b58e978
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865712B2

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