Sodium Hydroxide → 1-cyclobutyl-6-hydroxy-1H-indole-3-carbonitrile

HRID 1027990Notes

Reaction equation

[CH:1]1([N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:14]C)[CH:12]=3)[C:7]([C:16]#[N:17])=[CH:6]2)[CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[CH:1]1([N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([OH:14])[CH:12]=3)[C:7]([C:16]#[N:17])=[CH:6]2)[CH2:2][CH2:3][CH2:4]1

Participants

Conditions

Temperature: -20 °C

Procedure

1-cyclobutyl-6-methoxy-1H-indole-3-carbonitrile (100 g, 442 mmol) was dissolved in CH2Cl2 (700 mL) and cooled to −20° C. Boron tribromide (300 g, 1.2 mol) was added dropwise over 2.5 hours to the cooled solution. The reaction was poured into ice water (2 L), neutralized to pH 7 with 5 N aq. sodium hydroxide and stirred overnight at room temperature. The remaining organic solvent was evaporated and the resulting suspension was filtered. The solid was washed with water (2×200 mL), 1/1 hexane/ethyl ether (2×125 mL) and dried in a stream of nitrogen to give 1-cyclobutyl-6-hydroxy-1H-indole-3-carbonitrile as a beige powder (90.0 g, 96%).

Workup

customThe remaining organic solvent was evaporated
filtrationthe resulting suspension was filtered
washThe solid was washed with water (2×200 mL), 1/1 hexane/ethyl ether (2×125 mL)
customdried in a stream of nitrogen

Sources & evidence

ORD record: ord-54adaa327cce4a50a39ce75f6ce107bc
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735414B2

Reaction notes

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