Tetrahydrofuran → HCID 57932972, compound

HRID 1432632Notes

Reaction equation

HRID 1432632 reaction equation
Br[C:2]1[S:6][C:5]([CH3:7])=[C:4]([C:8]2[N:12]3[N:13]=[C:14]([CH3:22])[CH:15]=[C:16]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:11]3=[N:10][C:9]=2[CH3:23])[CH:3]=1.[I-].[C:25]1([Zn+])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1COCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:18]([CH:17]([C:16]1[C:11]2[N:12]([C:8]([C:4]3[CH:3]=[C:2]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[S:6][C:5]=3[CH3:7])=[C:9]([CH3:23])[N:10]=2)[N:13]=[C:14]([CH3:22])[CH:15]=1)[CH2:20][CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 57932944HCID 57932944, compoundHCID 178506617HCID 178506617, compound

Product 1

HCID 57932972HCID 57932972, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

Using a procedure similar to Example 32, from 3-(5-bromo-2-methyl-thiophen-3-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.20 g, 0.51 mmol) and PdCl2(dppf) (0.019 g, 0.025 mmol) and 0.5 M solution of phenylzinc iodide in THF (2.0 mL, 1.02 mmol). The residue is purified by column chromatography (0-10% EtOAc/hexane gradient) and is chromatographed (50×250 C18 Symmetry column, 30-70% water: 0.1% TFA/ACN: 0.1% TFA gradient) furnish the title compound (0.081 g, 0.21 mmol, 41%). 1H NMR (CDCl3), δ 0.90 (t, J=7.5 Hz, 6H), 1.75-1.94 (m, 4H), 2.40 (s, 3H), 2.48 (s, 3H), 2.52 (s, 3H), 3.32-3.41 (m, 1H), 6.66 (s, 1H), 7.23-7.30 (m, 1H), 7.32 (s, 1H), 7.34-7.41 (m, 2H), 7.57-7.63 (m, 2H). LC/MS (m/z): calcd. for C24H27N3S (M+H)+: 390.2; found: 390.2.

Workup

  1. customThe residue is purified by column chromatography (0-10% EtOAc/hexane gradient)
  2. customis chromatographed (50×250 C18 Symmetry column, 30-70% water: 0.1% TFA/ACN: 0.1% TFA gradient)

Sources & evidence

ORD record
ord-5e8f64e1854b4ef293cf6a4370e2dc6a
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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