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

HRID 2085674Notes

Reaction equation

HRID 2085674 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-212a560fa5194d93baf423a847688fed
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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