Lithium Hexamethyldisilazide → HCID 25005524, compound

HRID 2196109Notes

Reaction equation

HRID 2196109 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:28]2[O:27][CH2:26][C:21]3([O:25][CH2:24][CH2:23][O:22]3)[CH2:20][O:19][C:18]=2[C:17]([O:29][CH3:30])=[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:28]2[O:27][CH2:26][C:21]3([O:25][CH2:24][CH2:23][O:22]3)[CH2:20][O:19][C:18]=2[C:17]([O:29][CH3:30])=[CH:16][CH:15]=1)=[O:11]

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 109538273,5-Dichloro-4-methylpyridineHCID 59286712HCID 59286712, compound

Product 1

HCID 25005524HCID 25005524, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure, condensation of 3,5-dichloro-4-methylpyridine (53 mg, 0.33 mmol) with compound 518 (74 mg, 0.25 mmol) in THF (1.5 mL) in the presence of LiHMDS (0.75 mL, 0.75 mmol) afforded compound 126 as a white solid material after purification by column chromatography (60-80% EtOAc in light petroleum). LC-MS: RT=3.63 min.; m/z 426.18, 428.16 (M+H)+. 1H NMR (DMSO-d6): δ 8.64 (2H, s), 7.39 (1H, d, J 8.8), 6.86 (1H, d, J 8.9), 4.60 (2H, s), 4.34 (2H, s), 4.17 (2H, s), 3.97 (4H, s), 3.84 (3H, s).

Sources & evidence

ORD record
ord-b017146ef87e49f3b30c7492777cb071
Source dataset
uspto-grants-2012_12
Patent number
US08338431B2

Reaction notes

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