Sodium hydride → HCID 57537522, compound

HRID 1693696Notes

Reaction equation

[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:9][CH:10]=[CH:11][C:4]=12.[H-].[Na+].[CH:16]([Si:19](Cl)([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])([CH3:18])[CH3:17]>O1CCCC1>[F:13][C:2]([F:12])([F:1])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[N:9]([Si:19]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:16]([CH3:18])[CH3:17])[CH:10]=[CH:11][C:4]=12

Participants

Conditions

Temperature: 0 °C

Procedure

4-Trifluoromethyl-1H-pyrrolo[2,3-b]pyridine (1.5 g, 8 mmol) was suspended in tetrahydrofuran (20 mL) and cooled to 0° C. Sodium hydride (390 mg, 9.7 mmol) was added in small portions and the mixture was stirred at 0° C. for 1 h. Triisopropylsilyl chloride (2.6 mL, 12 mmol) was added and the mixture was stirred at 23° C. for 12 h. The reaction was quenched with saturated ammonium chloride solution (10 mL) and diluted with water (5 mL). The mixture was applied to a Varian chemelut cartridge and eluted with ethyl acetate. Purification by flash silica gel chromatography using a gradient of dichloromethane in hexanes afforded 4-Trifluoromethyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (2.5 g, 7.3 mmol, 90% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.44 (d, J=5 Hz, 1H), 7.76 (d, J=4 Hz, 1H), 7.44 (d, J=5.5 Hz, 1H), 6.74 (m, 1H), 1.88 (septet, J=7.5 Hz, 3H), 1.05 (d, J=7.5 Hz, 18H). MS: m/z 343.2 (M+H+).

Workup

stirringthe mixture was stirred at 23° C. for 12 h
customThe reaction was quenched with saturated ammonium chloride solution (10 mL)
additiondiluted with water (5 mL)
washeluted with ethyl acetate
customPurification by flash silica gel chromatography

Sources & evidence

ORD record: ord-625e60ed907d4cfc902b09cc14a3e7d2
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158647B2

Reaction notes

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