Sodium hydride → HCID 178474147, compound

HRID 2250392Notes

Reaction equation

[Cl-].[Br:2][C:3]1[CH:4]=[C:5]2[N:11]=[C:10]([CH2:12][P+](CCCC)(CCCC)CCCC)[NH:9][C:6]2=[N:7][CH:8]=1.[H-].[Na+].[CH:28]([C:30]1[N:35]=[C:34]([NH:36][C:37](=[O:39])[CH3:38])[CH:33]=[C:32]([CH3:40])[CH:31]=1)=O>O1CCCC1>[Br:2][C:3]1[CH:4]=[C:5]2[N:11]=[C:10](/[CH:12]=[CH:28]/[C:30]3[N:35]=[C:34]([NH:36][C:37](=[O:39])[CH3:38])[CH:33]=[C:32]([CH3:40])[CH:31]=3)[NH:9][C:6]2=[N:7][CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

5.0 g of 6-brom-3H-midazo[4,5-b]pyridin-2-yl-methyl-tributyl-phosphonium-chloride (compound A5) are suspended in 50 ml of tetrahydrofuran and added to a suspension of sodium hydride (60% strength) in 50 ml tetrahydrofuran at room temperature. After vigorously stirring for 10 min, 1.43 g of N-(6-formyl-4-methyl-pyridin-2-yl)-acetamide (compound B11) is added in portions (10 min). Subsequently, the suspension is heated at 90° C. for 22 h. Thereafter, the mixture is filtered with suction and the remaining residue is rinsed with tetrahydrofuran. The pure title compound is obtained by evaporating the filtrate to dryness to afford 1.88 g of an amorphous solid. M.p. >350° C. ESI-MS: 372.1/374.1 (MH+; 99%/100%). TLC: Rf=0.50 (dichloromethane/methanol 10:1).

Workup

filtrationThereafter, the mixture is filtered with suction
washthe remaining residue is rinsed with tetrahydrofuran

Sources & evidence

ORD record: ord-cd51aa7d6326442991b8f198107c9256
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07317021B2

Reaction notes

Loading…