Propargyl alcohol → HCID 69099881、化合物

HRID 2251530ノート

反応式

HRID 2251530 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=2)[CH2:9][CH2:10][C:11]2[CH:25]=[CH:24][C:14]([O:15][C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=2)=[N:6][CH:7]=1.[CH2:38]([OH:41])[C:39]#[CH:40]>CCN(CC)CC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[OH:41][CH2:38][C:39]#[C:40][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:35])[F:36])=[CH:29][CH:28]=2)[CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:24][CH:25]=2)=[N:6][CH:7]=1

参加物

6

反応物 2

HCID 7859Propargyl alcoholHCID 59643326HCID 59643326、化合物

生成物 1

HCID 69099881HCID 69099881、化合物

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 8471Triethylamine溶媒

実験手順

A solution of ethyl 2-[4-(2-{(5-bromopyridin-2-yl)[4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (500 mg; 0.86 mmol) in 3 ml of Et3N was treated under nitrogen with tetrakis(triphenylphosphine)palladium (0) (99 mg; 0.086 mmol) and copper (I) iodide (16 mg; 0.086 mmol). After stirring at rt for 5 minutes, propargyl alcohol (72 mg; 1.29 mmol) was added and the mixture heated at 65C for 7 hr. Upon cooling the reaction mixture was concentrated and the residue was partitioned between ethyl acetate and 0.1N HCl. The organic phase was washed with 0.1N HCl and brine, dried over sodium sulfate and concentrated. Purification by radial chromatography using ethyl acetate-hexane mixtures (5–50% gradient) afforded ethyl 2-[4-(2-{[5-(3-hydroxyprop-1-ynyl)pyridin-2-yl][4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate.

後処理

  1. temperatureUpon cooling the reaction mixture
  2. concentrationwas concentrated
  3. customthe residue was partitioned between ethyl acetate and 0.1N HCl
  4. washThe organic phase was washed with 0.1N HCl and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification by radial chromatography

出典と根拠

ORDレコード
ord-53abb0d1cda648f6a7c080adcd44e6c5
出典データセット
uspto-grants-2008_01
特許番号
US07319104B2

反応ノート

読み込み中…