Tris(furan-2-yl)phosphane → HCID 17961349, compound

HRID 1785755Notes

Reaction equation

HRID 1785755 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:19]([NH2:22])(=[O:21])=[O:20])[CH:5]=[C:6]([N+:16]([O-:18])=[O:17])[C:7]=1[NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C([Sn](CCCC)(CCCC)[C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1)CCC.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>C(#N)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:10]1([CH2:9][NH:8][C:7]2[C:2]([C:28]3[N:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[CH:3][C:4]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:5][C:6]=2[N+:16]([O-:18])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 27632512-(Tributylstannyl)pyrimidineHCID 22730462HCID 22730462, compound

Product 1

HCID 17961349HCID 17961349, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of Example 26A (270 mg, 0.69 mmol), 2-(tributylstannyl)pyrimidine (305 uL, 0.83 mmol), Pd2(dba)3 (32 mg, 0.034 mmol), and tris-(2-furyl)phosphine (32 mg, 0.10 mmol) in acetonitrile (2 mL) was heated to reflux for 48 hours and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes to provide the desired product. MS (ESI(+)) m/e 392 (M+H)+.

Workup

  1. temperatureto reflux for 48 hours
  2. concentrationconcentrated
  3. customThe concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-7f888f52943b4b95a867c0ac158aa687
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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