Hydrochloric Acid → HCID 11595204, compound

HRID 475117Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:6]=[CH:5]2.CC1(C)CCCC(C)(C)N1.C[C:32]([O-:35])(C)C.[K+].[Li]CCCC.Cl.C1C[O:46]CC1>C(Cl)Cl.O>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([Si:11]([CH:15]([CH3:17])[CH3:16])([CH:18]([CH3:20])[CH3:19])[CH:12]([CH3:13])[CH3:14])[CH:6]=[CH:5][C:4]=2[C:3]=1[C:32]([OH:35])=[O:46]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 5-fluoro-1-(triisopropylsilyl)-1H-indole (2.5 g, 8.58 mmol), 2,2,6,6-tetramethylpiperidine (2.42 g, 17.15 mmol), potassium 2-methylpropan-2-olate (1.92 g, 17.15 mmol) in anhydrous THF (75 mL) under nitrogen at −78° C. was added dropwise a solution of n-BuLi in THF (1.6 M, 10.7 mL, 17.15 mmol) at a rate to maintain the internal reaction temperature below −70° C. The mixture was then stirred at −78° C. for 2 h. The reaction mixture was poured into a slurry of ice (100 g), water (200 mL), and DCM (100 mL). The pH of aqueous phase was adjusted to 4.0 with HCl (2 M). A precipitate was formed, which was filtered, washed with water (10 mL) and ethoxyethane (10 mL) to afford 5-fluoro-1-(triisopropylsilyl)-1H-indole-4-carboxylic acid as a white solid (580 mg, 20.2%). MS (ESI): m/z=336.2 [M+1]+.

Workup

temperatureto maintain the internal reaction temperature below −70° C
customA precipitate was formed
filtrationwhich was filtered
washwashed with water (10 mL) and ethoxyethane (10 mL)

Sources & evidence

ORD record: ord-ccf555a8307d4d24a4657c3b88363784
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637537B2

Reaction notes

Loading…