Dimethylformamide → HCID 69017910, compound

HRID 1821011Notes

Reaction equation

HRID 1821011 reaction equation
I[C:2]1[CH:3]=[C:4]([C:12]2[S:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=3[CH3:24])=[N:15][N:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[CH3:25][N:26](C=O)C>[C-]#N.[Zn+2].[C-]#N.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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:25]([C:2]1[CH:3]=[C:4]([C:12]2[S:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=3[CH3:24])=[N:15][N:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10])#[N:26]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 69019136HCID 69019136, compound

Product 1

HCID 69017910HCID 69017910, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

2-(3-Iodo-4-isopropyloxyphenyl)-5-(4-bromo-2-methyphenyl)-1,3,4-thiadiazole (0.78 mmol; 0.4 g, from Step A), zinc cyanide (0.47 mmol, 0.55 g), tris(dibenzylideneacetone)-dipalladium(0) (0.039 mmol, 0.036 g) and 1,1′-bis(diphenylphosphino)-ferrocene (0.094 mmol, 0.052 g) were dissolved in DMF (5 mL) and heated at 120° C. for 3 h. The reaction was concentrated in vacuo. Silica gel chromatography eluting with 10% EtOAc/hexanes yielded 0.25 g of the desired product. ESI-MS (m/z) 416.1; HPLC A: 4.22 min.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. washSilica gel chromatography eluting with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-6815d87d584049278d0f1acfa6d297dc
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

Loading…