Lithium Hexamethyldisilazide → HCID 25005170, compound

HRID 2196108Notes

Reaction equation

HRID 2196108 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:27]2[O:26][CH2:25][C:21]3([CH2:24][S:23][CH2:22]3)[CH2:20][O:19][C:18]=2[C:17]([O:28][CH3:29])=[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:27]2[O:26][CH2:25][C:21]3([CH2:24][S:23][CH2:22]3)[CH2:20][O:19][C:18]=2[C:17]([O:28][CH3:29])=[CH:16][CH:15]=1)=[O:11]

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 109538273,5-Dichloro-4-methylpyridineHCID 59286718HCID 59286718, compound

Product 1

HCID 25005170HCID 25005170, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure, condensation of 3,5-dichloro-4-methylpyridine (366 mg, 2.26 mmol) with compound 516 (516 mg, 1.74 mmol) in THF (10 mL) in the presence of LiHMDS (5.2 mL, 5.2 mmol) afforded compound 123 as a white solid material after purification by column chromatography (55-65% EtOAc in light petroleum). LC-MS: RT=4.23 min.; m/z 426.24, 428.25 (M+H)+, 424.23 (M−H)−. 1H NMR (CDCl3): δ 8.51 (2H, s), 7.57 (1H, d, J 9.2), 6.71 (1H, d, J 9.2), 4.64 (2H, s), 4.46 (2H, s), 4.33 (2H, s), 3.93 (3H, s), 3.20 (2H, d, J 9.9), 3.12 (2H, d, J 9.9).

Sources & evidence

ORD record
ord-90a82659f3b4428ca4b17af665d81ea4
Source dataset
uspto-grants-2012_12
Patent number
US08338431B2

Reaction notes

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