Water → 2-tert-Butyl-7-fluoro-5-nitro-1H-indole

HRID 1964299Notes

Reaction equation

[CH3:1][C:2]([CH3:22])([CH3:21])[C:3]#[C:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([F:14])[C:6]=1[NH:15]C(=O)CCC.CC([O-])(C)C.[K+].O>CN(C=O)C>[C:2]([C:3]1[NH:15][C:6]2[C:5]([CH:4]=1)=[CH:10][C:9]([N+:11]([O-:13])=[O:12])=[CH:8][C:7]=2[F:14])([CH3:22])([CH3:21])[CH3:1]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of N-[2-(3,3-dimethyl-but-1-ynyl)-6-fluoro-4-nitro-phenyl]-butyramide (3.2 g, 10 mmol) in DMF (20 mL) was added t-BuOK (2.3 g, 21 mmol) at room temperature. The mixture was heated at 120° C. for 2 g before being cooled down to room temperature. Water (50 mL) was added to the reaction mixture and the resulting mixture was extracted with CH2Cl2 (30 mL×3). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under vacuum to give 2-tert-butyl-7-fluoro-5-nitro-1H-indole (2.0 g, 81%), which was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 9.95 (brs, 1 H), 8.30 (d, J=2.1 Hz, 1 H), 7.74 (dd, J=1.8, 11.1 Hz, 1 H), 6.43 (dd, J=2.4, 3.3 Hz, 1 H), 1.43 (s, 9 H).

Workup

temperaturebefore being cooled down to room temperature
extractionthe resulting mixture was extracted with CH2Cl2 (30 mL×3)
dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
customevaporated under vacuum

Sources & evidence

ORD record: ord-bfbd00f92fd44408a7db4e1cfb0ebb8c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415387B2

Reaction notes

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