HCID 69020313, compound → HCID 68892584, compound

HRID 1821009Notes

Reaction equation

HRID 1821009 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:14][C:15](C3C=CC(Br)=CC=3C)=[N:16][N:17]=2)[CH:6]=[CH:7][C:8]=1[S:9][CH:10]([CH3:12])[CH3:11])#[N:2].[Br-].[CH2:27]([O:29][C:30](=[O:34])[CH2:31][CH2:32][Zn+])[CH3:28]>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:14][CH2:15][N:16]([C:8]3[CH:7]=[CH:6][C:5]([CH2:32][CH2:31][C:30]([O:29][CH2:27][CH3:28])=[O:34])=[CH:4][C:3]=3[CH3:1])[N:17]=2)[CH:6]=[CH:7][C:8]=1[S:9][CH:10]([CH3:11])[CH3:12])#[N:2]

Participants

4

Reactant 2

HCID 69020313HCID 69020313, compoundHCID 178471816HCID 178471816, compound

Product 1

HCID 68892584HCID 68892584, compound

Reagents, catalysts & solvents 1

HCID 178418851HCID 178418851, compoundCatalyst

Procedure

Bis(tri-tert-butylphosphine)palladium (0) (5 mg) was added to a solution of 2-(3-cyano-4-isopropylthiophenyl)-5-(4-bromo-2-methyphenyl)-1,3,4-thiadiazole (0.15 mmol, 0.066 g, from Step C) in 3-ethoxy-3-oxopropylzinc bromide (0.5M in TI-IF) (0.31 mmol, 0.61 mL) which had been degassed with argon. The reaction mixture was stirred under an atmosphere of argon at rt for 5 h after which it was concentrated in vacuo. Silica gel chromatography eluting with 20% EtOAc/hexane yielded the desired product. ESI-MS (m/z) 452.3; HPLC A: 2.85 min.

Workup

  1. customhad been degassed with argon
  2. concentrationwas concentrated in vacuo
  3. washSilica gel chromatography eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-96ae253b012a4e59ad1e09ec5a4f5ca4
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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