Hydrochloric Acid → HCID 22148991, compound

HRID 1451515Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH2:13][CH2:14][C:15]([OH:17])=[O:16].[Li]CCCC.[Br:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1.Cl>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[Br:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[C:6]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[C:7]2[CH3:12])=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold (-78° C.) solution of the indole from Step 1 (877 mg, 4.04 mmol) in 40 mL of THF and 2.5 mL of HMPA was added n-BuLi (1.45M solution in hexanes, 5.6 mL, 8.12 mmol), giving a thick slurry. The mixture was warmed to 0° C., then cooled to -78° C. A solution of p-bromobenzyl bromide (1.18 g, 4.72 mmol) in 8 mL of THF was then added, and the mixture was warmed to room temperature. After 30 min, the reaction was poured into 1M HCl and extracted with ether. The organic layer was washed thrice with water, then with brine, dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography (30% ethyl acetate/hexanes) to give 529 mg of the title compound as a crystaline solid.

Workup

customgiving a thick slurry
temperaturecooled to -78° C
temperaturethe mixture was warmed to room temperature
extractionextracted with ether
washThe organic layer was washed thrice with water
dry with materialwith brine, dried over MgSO4
filtrationfiltered
customevaporated
customThe residue was purified by flash chromatography (30% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-9da3e03f21694e729140c512b0c19270
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05604253

Reaction notes

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