Lithium Hexamethyldisilazide → HCID 25005526, compound

HRID 2196112Notes

Reaction equation

HRID 2196112 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].C[O:11][C:12]([C:14]1[C:31]2[O:30][CH2:29][C:21]3([CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23][CH2:22]3)[CH2:20][O:19][C:18]=2[C:17]([O:32][CH3:33])=[CH:16][CH:15]=1)=O.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[CH2:8][C:12]([C:14]1[C:31]2[O:30][CH2:29][C:21]3([CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23][CH2:22]3)[CH2:20][O:19][C:18]=2[C:17]([O:32][CH3:33])=[CH:16][CH:15]=1)=[O:11]

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 109538273,5-Dichloro-4-methylpyridineHCID 59286715HCID 59286715, compound

Product 1

HCID 25005526HCID 25005526, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure, condensation of 3,5-dichloro-4-methylpyridine (93 mg, 0.58 mmol) with compound 522 (150 mg, 0.44 mmol) in THF (2 mL) in the presence of LiHMDS (1.3 mL, 1.3 mmol) afforded compound 129 as a white solid material after purification by column chromatography (55-60% EtOAc in light petroleum). LC-MS: RT=3.95 min.; m/z 468.19, 470.23 (M+H)+, 466.36, 468.33 (M−H)−. 1H NMR (DMSO-d6): δ 8.65 (2H, s), 7.42 (1H, d, J 8.8), 6.89 (1H, d, J 9.1), 4.63 (2H, s), 4.33 (2H, s), 4.08 (2H, s), 3.84 (3H, s), 3.82 (4H, s), 1.39 (3H, s), 1.37 (3H, s).

Sources & evidence

ORD record
ord-e2501468134e4c33bc46a50666952b4b
Source dataset
uspto-grants-2012_12
Patent number
US08338431B2

Reaction notes

Loading…