HCID 46869088, compound → HCID 46869635, compound

HRID 1912477Notes

Reaction equation

HRID 1912477 reaction equation
Cl[C:2]1[C:7]2[N:8]=[C:9]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[N:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=3)[C:6]=2[N:5]=[C:4]([C:25]([OH:27])=[O:26])[CH:3]=1.[Cl-].[CH3:29][Zn+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:18][C:14]1[CH:13]=[C:12]([C:11]2[C:6]3[N:5]=[C:4]([C:25]([OH:27])=[O:26])[CH:3]=[C:2]([CH3:29])[C:7]=3[N:8]=[C:9]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[N:10]=2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 46869088HCID 46869088, compoundHCID 178477797HCID 178477797, compound

Product 1

HCID 46869635HCID 46869635, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 9 (30 mg; 0.08 mmol), Pd(PPh3)4 (4.5 mg) and 2M methylzinc chloride (0.16 mL, 0.31 mmol) in THF (5 mL) was stirred at 80° C. for 16 hours then concentrated in vacuo. The residue was partitioned between EA and aq. citric acid and the two phases separated. The aqueous layer was dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (EA/EtOH/AcOH, 90/10/1) afforded the title compound as a yellow solid.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was partitioned between EA and aq. citric acid
  3. customthe two phases separated
  4. dry with materialThe aqueous layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by column chromatography (EA/EtOH/AcOH, 90/10/1)

Sources & evidence

ORD record
ord-5f9ae9b30608415ab7c5bce4e6cd566d
Source dataset
uspto-grants-2013_12
Patent number
US08609666B2

Reaction notes

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