Methyl iodide → HCID 86689563, compound

HRID 1853903Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]2)[CH:5]=[CH:4][C:3]=1[CH:17]([CH:27]([CH3:29])[CH3:28])[CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23].CI.[CH3:32][Si]([N-][Si](C)(C)C)(C)C.[Na+]>>[F:1][C:2]1[CH:7]=[C:6]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:15])([CH3:16])[O:9]2)[CH:5]=[CH:4][C:3]=1[CH:17]([CH:27]([CH3:29])[CH3:28])[CH2:18][N:19]([CH3:32])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 2724254Sodium bis(trimethylsilyl)amide

HCID 86689564HCID 86689564, compound

Product 1

HCID 86689563HCID 86689563, compoundYield 96.4%

Procedure

Following the procedure described for Example 647, tert-butyl 2-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-methylbutylcarbamate (650 mg, 1.6 mmol) was reacted with methyl iodide (1M solution in toluene, 3.2 mL, 3.2 mmol) and NaHMDS (1 M solution, 4.8 mL, 4.8 mmol) to afford the desired product (650 mg, 94%) as viscous mass. ESI MS m/z 421 [C23H38FBNO4+H]+

Sources & evidence

ORD record: ord-bd936d9f03e74a698d82ecc6103b1915
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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