N-bromobutanimide → tert-Butyl 1-(1-(3,5-difluorobenzyl)-5-bromo-1H-imidazol-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethylcarbamate

HRID 2099814Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:39]=[C:40]([F:42])[CH:41]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH:11]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:12][C:13]1[CH:21]=[C:20]([CH3:22])[C:19]2[C:15](=[CH:16][N:17]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[N:18]=2)[CH:14]=1.[Br:43]N1C(=O)CCC1=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:39]=[C:40]([F:42])[CH:41]=1)[CH2:5][N:6]1[C:10]([Br:43])=[CH:9][N:8]=[C:7]1[CH:11]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[CH2:12][C:13]1[CH:21]=[C:20]([CH3:22])[C:19]2[C:15](=[CH:16][N:17]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:28])([CH3:29])[CH3:30])[N:18]=2)[CH:14]=1

Participants

Conditions

Temperature: -78 °C

Procedure

tert-Butyl 1-(1-(3,5-difluorobenzyl)-1H-imidazol-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethylcarbamate (72.0 mg, 0.12 mmol) was dissolved in methylene chloride (3.0 mL) and cooled to −78° C. To this was added N-bromosuccinimide (18.3 mg, 0.11 mmol) and the mixture allowed to stir at −78° C. for 30 min. After warming to room temperature, the solvent was removed and the residue purified by column chromatography to afford 30 mg (40%). 1H-NMR (CD3OD, 300 MHz) δ −0.06 (s, 9H), 0.89 (m, 2H), 1.33 (s, 9H), 2.44 (s, 3H), 3.15-3.25 (m, 1H), 3.57-3.66 (m, 2H), 4.80-5.09 (m, 2H), 6.26 (m, 2H), 6.47-6.66 (m, 2H), 7.12 (s, 1H), 7.20 (s, 1H), 7.91 (s, 1H). Mass spec.: 678.3 (MH)+.

Workup

temperatureAfter warming to room temperature
customthe solvent was removed
customthe residue purified by column chromatography
customto afford 30 mg (40%)

Sources & evidence

ORD record: ord-544246db49574ab58e26ada29f04546d
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569578B2

Reaction notes

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