Triphenylphosphine → Triphenylphosphine Oxide

HRID 538344ノート

反応式

HRID 538344 の反応式
[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]

参加物

5

反応物 2

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)+].

後処理

  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

出典と根拠

ORDレコード
ord-ce7f7842e1ea4eb9873c05b84b58e978
出典データセット
uspto-grants-2014_10
特許番号
US08865712B2

反応ノート

読み込み中…