Phosphorus oxychloride → HCID 69056328, compound

HRID 1819688Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=O)[NH:12]C(C)(C)C)=[C:5]2[CH2:18][C:19]([O:21][CH3:22])=[O:20].O=P(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]#[N:12])=[C:5]2[CH2:18][C:19]([O:21][CH3:22])=[O:20]

Participants

Conditions

Temperature: 80 °C

Procedure

Step J (1): To a solution of methyl 2-(5-bromo-2-(tert-butylcarbamoyl)-1H-indol-3-yl)acetate (124 mg, 0.34 mmol) in toluene was added POCl3 (182 mg, 1.19 mmol). The mixture was stirred at 80° C. for 6 h. The solvent was removed. The product was isolated by flash chromatography to give 50 mg of methyl 2-(5-bromo-2-cyano-1H-indol-3-yl)acetate (yield 50.2%). MS (ESI) (M+H)+=295.03. 1H NMR (500 MHz, CDCl3) δ ppm 3.77 (s, 3 H) 3.89 (s, 2 H) 7.11 (d, J=8.85 Hz, 1 H) 7.36 (dd, J=8.85, 1.83 Hz, 1 H) 7.72 (d, J=1.83 Hz, 1 H) 9.00 (s, 1 H).

Workup

customThe solvent was removed
customThe product was isolated by flash chromatography

Sources & evidence

ORD record: ord-5ac90ec71875418790c0f1826849de5c
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601751B2

Reaction notes

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