Sodium hydride → HCID 131717002, compound

HRID 345416Notes

Reaction equation

HRID 345416 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:9]=[C:8]2[N:10]=[C:11]([CH2:13][CH3:14])[NH:12][C:7]2=[C:6]([CH3:15])[CH:5]=1.[C:16]1([C:22]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[N:23]2[C:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]3[CH:39]=[CH:38][C:37]([CH2:40]Br)=[CH:36][CH:35]=3)=[N:26][N:25]=[N:24]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[CH3:3][C:4]1[N:9]=[C:8]2[N:10]([CH2:40][C:37]3[CH:36]=[CH:35][C:34]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[C:27]4[N:23]([C:22]([C:48]5[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=5)([C:42]5[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=5)[C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=5)[N:24]=[N:25][N:26]=4)=[CH:39][CH:38]=3)[C:11]([CH2:13][CH3:14])=[N:12][C:7]2=[C:6]([CH3:15])[CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 98153742,6-Dimethyl-8-ethyl-1-deazapurineHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazole

Product 1

HCID 131717002HCID 131717002, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of NaH (17.2 mmol of an 80% dispersion) in dry dimethylformamide (30 mL) at rt was added 5.7-dimethyl-2-ethylimidazo[4,5-b]pyridine (1.51 g, 8.62 mmol) in one portion. After 20 minutes, the mixture was cooled to 0° C. and N-triphenylmethyl-5-(4'-bromomethylbiphenyl-2-yl)-tetrazole (5.29 g, 9.48 mmol) was added in one portion. The resulting mixture was warmed to rt and stirred for 15 hours. The excess NaH was quenched with water and the bulk of the DMF was removed in vacuo at 40°-50° C. The residue was extracted with EtOAc from brine, dried (K2CO3), and concentrated. Purification by flash chromatography (SiO2, solvent gradient: 80% EtOAc/hexanes, 100% EtOAc) gave 4.25 g of 5,7-dimethyl-2-ethyl-3-(2'-(N-triphenylmethyltetrazol-5-yl)biphen-4-yl)methyl-3H-imidazo[4,5-b]pyridine: 1H NMR (300 MHz, CDCl3) δ7.86 (dd, 1H, J=7, 2 Hz), 750-7.41 (m, 2H), 7.36-721 (m, 10 H), 7.05 (d, 2 H, J=4.5 Hz), 6.95-6.89 (m, 7 H), 6.86 (d, 2 H, J=4.5 Hz), 5.35 (s, 2H), 2.67 (q, 2 H, J=7.5 Hz), 2.65 (s, 3 H), 2.58 (s, 3 H), 1.25 (t, 3 H, J=7.5 Hz).

Workup

  1. temperatureThe resulting mixture was warmed to rt
  2. customThe excess NaH was quenched with water
  3. customthe bulk of the DMF was removed in vacuo at 40°-50° C
  4. extractionThe residue was extracted with EtOAc from brine
  5. dry with materialdried (K2CO3)
  6. concentrationconcentrated
  7. customPurification by flash chromatography (SiO2, solvent gradient: 80% EtOAc/hexanes, 100% EtOAc)

Sources & evidence

ORD record
ord-1c9fd8a6ea004118bfd23f3ec0c907bf
Source dataset
uspto-grants-1991_10
Patent number
US05057522

Reaction notes

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