Chlorosuccinimide → tert-butyl-N-{1-[(4-bromo-5-chloro-6-{2-[tris(propan-2-yl)silyl]ethynyl}-pyridin-2-yl)carbamoyl]ethyl}-N-methylcarbamate

HRID 923661Notes

Reaction equation

[C:1]([O:5][C:6](=[O:33])[N:7]([CH:9]([C:11](=[O:32])[NH:12][C:13]1[CH:18]=[C:17]([Br:19])[CH:16]=[C:15]([C:20]#[C:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[N:14]=1)[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[Cl:34]N1C(=O)CCC1=O>C(#N)C>[C:1]([O:5][C:6](=[O:33])[N:7]([CH:9]([C:11](=[O:32])[NH:12][C:13]1[CH:18]=[C:17]([Br:19])[C:16]([Cl:34])=[C:15]([C:20]#[C:21][Si:22]([CH:23]([CH3:24])[CH3:25])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[N:14]=1)[CH3:10])[CH3:8])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of (1-{4-Bromo-6-[(triisopropylsilanyl)-ethynyl]-pyridin-2-ylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester C1 (50 mg, 930 μmol), N-chlorosuccinimide (12 mg, 0.90 mmol) and ACN (1 ml) is stirred at 50° C. for 17 h. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 11 mg (21%). HPLC-MS: M+H=574/572; tR=2.04 min (METHOD—1).

Workup

concentrationThe mixture is concentrated in vacuo
customthe product purified by RP HPLC

Sources & evidence

ORD record: ord-4ed04e97699a40b89e2529a4391aec78
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278978B2

Reaction notes

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