Tetrahydrofuran → HCID 178437418, compound

HRID 1729438Notes

Reaction equation

HRID 1729438 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]4[NH:30][N:29]=[N:28][N:27]=4)=[CH:16][CH:15]=3)C(CC)=[N:10][C:5]2=[C:4]([CH3:31])[CH:3]=1.[CH:32]([Mg]Cl)([CH3:34])[CH3:33].[CH2:37]1[CH2:41]OC[CH2:38]1>[Cl-].[Cl-].[Zn+2]>[CH2:32]([C:34]1[N:8]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[NH:30][N:29]=[N:28][N:27]=3)=[CH:18][CH:19]=2)[C:6]2=[N:7][C:2]([CH:37]([CH3:41])[CH3:38])=[CH:3][C:4]([CH3:31])=[C:5]2[N:10]=1)[CH3:33]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 178418918HCID 178418918, compoundHCID 178437403HCID 178437403, compound

Product 1

HCID 178437418HCID 178437418, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

To 5-bromo-2-ethyl -7-methyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-3H-imidazo-[4,5-b]pyridine (75 mg) in THF (2 mL) at -78° C. was sequentially added ZnCl2 (1.58 mL, 1M/ether), iso-propylmagnesium chloride (0.79 mL, 2M/ether), and tetrakis-triphenylphosphinepalladium (15 mg). After complete addition the reaction was warmed to RT and stirred for 16 hours. Extractive workup (EtOAc, from dilute HOAc), and purification (SiO2, 80/20/1 CH2Cl2 /MeOH/NH4OH) gave 43 mg of a solid. 1H NMR (300 MHz, CD3OD) δ 7.60-7.50 (m, 2 H), 7.45 (t, 2H, J=6.9 Hz), 7.12-7.00 (m, 5H), 5.50 (s, 2H), 3.10 (quintet, 1H, J=6.9 Hz) 2.84 (q, 2H, J=7.5 Hz), 2.59 (s, 3H), 1.31 (d, 6H, J=6.9 Hz), 1.24 (t, 3H, J=7.5 Hz)

Workup

  1. customat -78° C.
  2. additionAfter complete addition the reaction
  3. customExtractive workup (EtOAc, from dilute HOAc), and purification (SiO2, 80/20/1 CH2Cl2 /MeOH/NH4OH)

Sources & evidence

ORD record
ord-249b79f032a742d380dd36f0aefa4c3c
Source dataset
uspto-grants-1994_07
Patent number
US05332744

Reaction notes

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