Sodium hydride → HCID 67942964, compound

HRID 1729397Notes

Reaction equation

HRID 1729397 reaction equation
[CH2:1]([C:4]1[NH:5][C:6]2[C:7]([N:12]=1)=[N:8][CH:9]=[CH:10][CH:11]=2)[CH2:2][CH3:3].[C:13]1([C:19]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:20]2[C:24]([C:25]3[C:30]([C:31]4[CH:36]=[CH:35][C:34]([CH2:37]Br)=[CH:33][CH:32]=4)=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:23][N:22]=[N:21]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+]>CCOC(C)=O>[CH2:1]([C:4]1[N:12]([CH2:37][C:34]2[CH:33]=[CH:32][C:31]([C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:24]3[N:20]([C:19]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:21]=[N:22][N:23]=3)=[CH:36][CH:35]=2)[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[N:5]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 124677082-Propylimidazo[4,5-b]pyridine

Product 1

HCID 67942964HCID 67942964, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-propyl-3-(2'-(N-triphenylmethyltetrazol-5-yl)-biphen-4-yl)methyl-3H-imidazo[4,5-b]pyridine was prepared according to the procedure described in Example 7, Part A from 2-propylimidazo[4,5-b]pyridine (19 mg, 0.118 mmol), N-triphenylmethyl-5-(4'-bromomethylbiphen-2-yl)tetrazole (60 mg, 0.108 mmol), and NaH (0.236 mmol). Yield: 18 mg (26%) thick oil; Rf: 0.75 (SiO2 tic, 100% EtOAc); 1H NMR (300 MHz, CDCl3) δ 8.27 (dd, 1H, J=6, 1 Hz), 8.01 (dd, 1H, J=9, 1 Hz), 7.85 (dd, 1H, J=9, 1.5 Hz), 7.50-7.42 (m, 2H), 7.38-7.22 (m, 11H), 7.08 (d, 2H J=7 Hz), 6.98-6.88 (m, 7H), 5.40 (s, 2H), 2.66 (t, 2H, J=7.5 Hz), 1.80-1.65 (m, 2H), 0.93 (t, 3H, J=6 Hz).

Sources & evidence

ORD record
ord-b2bb59c4eee246869cc57bf4effae6b7
Source dataset
uspto-grants-1994_07
Patent number
US05332744

Reaction notes

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