Butyl vinyl ether → HCID 68845177, compound

HRID 1725337Notes

Reaction equation

HRID 1725337 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:20][CH3:21])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2OS(C(F)(F)F)(=O)=O.[CH:22]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH2:23].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:25]([O:24][C:22]([C:7]1[C:6]2[C:11](=[C:2]([F:1])[CH:3]=[C:4]([O:20][CH3:21])[CH:5]=2)[N:10]=[CH:9][CH:8]=1)=[CH2:23])[CH2:26][CH2:27][CH3:28]

Participants

7

Reactant 4

HCID 8108Butyl vinyl etherHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 85806400HCID 85806400, compound

Product 1

HCID 68845177HCID 68845177, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

15.5 g (47.5 mmol) of 1,1,1-Trifluoro-methanesulfonic acid 8-fluoro-6-methoxy-quinolin-4-yl ester, 24.5 mL (0.19 mol) of butyl vinyl ether and 13.3 mL of triethylamine were takent up in 100 mL of DMF. 2.0 g (4.75 mmol) of dppp (1,3-bis(diphenylphosphino)propane) and 1.06 g (4.75 mmol) of Pd(OAc)2 were added and the contents heated to 60 C for 4 hrs. No starting material remained. Contents were rotary-evaporated to remove as much DMF as possible. Crude material was purified by flash chromatography on silica gel using 10% ethyl acetate/hexanes as the eluent to give 9.0 g (69%) of the desired product. 1H NMR (CDCl3, 400 MHz) 8.78 (d, 1H), 7.43 (d, 1H), 7.28 (m, 1H), 7.09 (d, 1H), 4.58 (d, 1H), 4.50 (d, 1H), 3.96 (t, 2H), 3.90 (s, 3H), 1.80 (m, 2H), 1.53 (m, 2H), 0.97 (t, 3H LCMS (M+H)+ 276.

Workup

  1. temperaturethe contents heated to 60 C for 4 hrs
  2. customContents were rotary-evaporated
  3. customto remove as much DMF as possible
  4. customCrude material was purified by flash chromatography on silica gel using 10% ethyl acetate/hexanes as the eluent

Sources & evidence

ORD record
ord-384d34776cc547a091d4716cb0a977fc
Source dataset
uspto-grants-2009_02
Patent number
US07491714B2

Reaction notes

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