5-fluoro-2-[1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-oxazolo[5,4-b]pyridine → 5-fluoro-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)-oxazolo[5,4-b]pyridine

HRID 40722Notes

Reaction equation

[F:1][C:2]1[N:7]=[C:6]2[O:8][C:9]([C:11]3[CH:12]=[C:13]4[CH:19]=[CH:18][N:17](CC5C=CC(OC)=CC=5)[C:14]4=[N:15][CH:16]=3)=[N:10][C:5]2=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[F:1][C:2]1[N:7]=[C:6]2[O:8][C:9]([C:11]3[CH:12]=[C:13]4[CH:19]=[CH:18][NH:17][C:14]4=[N:15][CH:16]=3)=[N:10][C:5]2=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 170 °C

Procedure

Crude 5-fluoro-2-[1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-oxazolo[5,4-b]pyridine from Step 2 was dissolved in TFA (0.5 mL) and heated by microwave to 170° C. for 25 min. The volatiles were then removed in vacuo and the resulting residue was purified by HPLC to afford 5-fluoro-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)-oxazolo[5,4-b]pyridine (2.5 mg, 9.8 μmol, 6% yield). ES MS (M+H+)=255; 1H NMR δ (ppm) (DMSO-d6): 12.18 (1H, s), 9.04 (1H, d, J=2.10 Hz), 8.76 (1H, d, J=2.06 Hz), 8.44 (1H, dd, J=8.39, 7.10 Hz), 7.67 (1H, t, J=2.75 Hz), 7.31 (1H, d, J=8.40 Hz), 6.68 (1H, d, J=3.43 Hz); HRMS m/z 255.0675 (C13H7FN4O+H+ requires 255.0677).

Workup

customThe volatiles were then removed in vacuo
customthe resulting residue was purified by HPLC

Sources & evidence

ORD record: ord-8d0bcf1766954255b647c761a9fbe553
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530483B2

Reaction notes

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