1,3-Bis(diphenylphosphino)propane → HCID 67217142、化合物

HRID 219411ノート

反応式

HRID 219411 の反応式
C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:31]1[C:39]2[C:34](=[N:35][CH:36]=[C:37]([C:40]3[CH:41]=[C:42]([CH:50]=[CH:51][C:52]=3[CH3:53])[C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH:38]=2)[O:33][C:32]=1[C:54]1[CH:59]=[CH:58][C:57]([F:60])=[CH:56][CH:55]=1>CO.CS(C)=O.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:46]([O:45][C:43]([C:42]1[CH:50]=[CH:51][C:52]([CH3:53])=[C:40]([C:37]2[CH:38]=[C:39]3[C:31]([C:43]([O:45][CH3:46])=[O:44])=[C:32]([C:54]4[CH:55]=[CH:56][C:57]([F:60])=[CH:58][CH:59]=4)[O:33][C:34]3=[N:35][CH:36]=2)[CH:41]=1)=[O:44])([CH3:48])([CH3:49])[CH3:47]

参加物

7

反応物 2

HCID 812191,3-Bis(diphenylphosphino)propaneHCID 67217138Tert-butyl 3-(3-bromo-2-(4-fluorophenyl)furo[2,3-b]pyridin-5-yl)-4-methylbenzoate

生成物 1

HCID 67217142HCID 67217142、化合物収率 190.8%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 679Dimethyl Sulfoxide溶媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1,3-bis(diphenylphosphino)propane (119 mg, 0.287 mmol) was added to a stirring solution of palladium(II) acetate (32 mg, 0.144 mmol) and tert-butyl 3-(3-bromo-2-(4-fluorophenyl)furo[2,3-b]pyridin-5-yl)-4-methylbenzoate (231 mg, 0.479 mmol) in MeOH (1.6 mL) and DMSO (3 mL) at 80° C. in a PARR bomb which was then charged with 300 psi CO (g) and allowed to stir overnight. The mixture was diluted with EtOAc and filtered through a pad of celite. The filtrate was washed with sat. aq. NaHCO3, and brine. The organic phase was dried over Na2SO4, filtered and concentrated to give the expected product methyl 5-(5-(tert-butoxycarbonyl)-2-methylphenyl)-2-(4-fluorophenyl)furo[2,3-b]pyridine-3-carboxylate (211 mg, 0.457 mmol, 95% yield) crude by LCMS which was used directly in the next step. LC-MS retention time: 2.32 min; m/z (MH+): 462. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters XBridge 5u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 3 mM, a hold time of 1 mM, and an analysis time of 4 min where solvent A was 5% MeOH/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% MeOH/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode.

後処理

  1. additionwas then charged with 300 psi CO (g)
  2. filtrationfiltered through a pad of celite
  3. washThe filtrate was washed with sat. aq. NaHCO3, and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-b65333a5e3cc4a7c8895235f01802ab2
出典データセット
uspto-grants-2012_06
特許番号
US08198449B2

反応ノート

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