Methanol → HCID 67131400, compound

HRID 906876Notes

Reaction equation

HRID 906876 reaction equation
C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:47][C:48]1[CH:49]=[C:50](B(O)O)[CH:51]=[CH:52][C:53]=1[F:54].CO.[CH2:60]([N:67]1[CH2:71][CH:70]=[C:69]([C:72](=[O:74])[CH3:73])[CH2:68]1)[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>O>[CH2:60]([N:67]1[CH2:71][C@H:70]([C:50]2[CH:51]=[CH:52][C:53]([F:54])=[C:48]([Cl:47])[CH:49]=2)[C@@H:69]([C:72](=[O:74])[CH3:73])[CH2:68]1)[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 634876Binap, (A+-)-HCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 57576371(1-Benzyl-2,5-dihydro-1H-pyrrol-3-yl)-ethanone

Product 1

HCID 67131400HCID 67131400, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A two necked flask was charged under argon with rhodium(acac)bis ethylene (31 mg, 0.05 eq.), (R)-BINAP (76 mg, 0.05 eq.) and 3-chloro-4-fluoro-phenylboronic acid (850 mg, 2.0 eq.). 60 mL of MeOH and 6.0 mL of H2O were added followed by 1-(1-benzyl-2,5-dihydro-1H-pyrrol-3-yl)-ethanone. The reaction mixture was heated at 60° C. for 2 hours, cooled down to RT and concentrated under vacuo. Purification by flash chromatography (SiO2, EtOAc/Heptane 2/1) afforded 180 mg (22%) of the title product as a light yellow oil.

Workup

  1. temperaturecooled down to RT
  2. concentrationconcentrated under vacuo
  3. customPurification by flash chromatography (SiO2, EtOAc/Heptane 2/1)

Sources & evidence

ORD record
ord-85d2ebde2c394e8d88aaf3bb8e55f70a
Source dataset
uspto-grants-2011_09
Patent number
US08012998B2

Reaction notes

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