Methyl iodide → HCID 89601551, compound

HRID 869069Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[C:15]3[C:11](=[N:12][N:13]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])[C:14]=3[CH:24]([CH3:26])[CH3:25])[C:10]2=[O:35])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:36][Si]([N-][Si](C)(C)C)(C)C.[K+].CI>>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:16]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)([CH3:36])[C:15]3[C:11](=[N:12][N:13]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])[C:14]=3[CH:24]([CH3:26])[CH3:25])[C:10]2=[O:35])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 3251421Potassium bis(trimethylsilyl)amide

HCID 89601326HCID 89601326, compound

Product 1

HCID 89601551HCID 89601551, compound

Procedure

The title compound was prepared in analogy to the procedure described for example 74 but using the compound prepared in example 88, 3 equivalents of KHMDS and 2 equivalents of methyl iodide. The reaction mixture was stirred for 2 h at rt. The crude material was purified by silica gel column chromatography (hexane/EtOAc, 4:1) followed by preparative HPLC (Column: AG/PP/C-18-15/025. Flow: 20 mL/min. Gradient: 25% B; A=0.1% TFA in water, B=acetonitrile/MeOH, 1:1). tR: 6.92 min (HPLC 2); ESI-MS: 524.1 [M+H]+ (LC-MS 2).

Workup

customThe crude material was purified by silica gel column chromatography (hexane/EtOAc, 4:1)

Sources & evidence

ORD record: ord-b9b6325655ff42fb8102a38c3d1cbf0a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969341B2

Reaction notes

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