Sodium Hydroxide → 5-(2,3-dihydro-benzofuran-5-yl)-3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 2114065Notes

Reaction equation

C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:20]=[CH:21][C:22]5[O:26][CH2:25][CH2:24][C:23]=5[CH:27]=4)[CH:18]=[C:13]3[C:12]([C:28]3[CH:29]=[N:30][NH:31][CH:32]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>CCO>[O:26]1[C:22]2[CH:21]=[CH:20][C:19]([C:17]3[CH:18]=[C:13]4[C:12]([C:28]5[CH:32]=[N:31][NH:30][CH:29]=5)=[CH:11][NH:10][C:14]4=[N:15][CH:16]=3)=[CH:27][C:23]=2[CH2:24][CH2:25]1

Participants

Conditions

Temperature: 85 °C

Procedure

To 49 (45 mg, 0.10 mmol) in EtOH (3 mL) was added 10% aq. NaOH (1.25 mL) and the reaction mixture was heated at 85° C. for 1 h. The mixture was concentrated to afford a yellow solid. Purification by preparative LCMS (column LUNA 10μ C18(2) 00G-4253-V0 250×50 mm) using water—acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) afforded the product 50 (16 mg, 53%) as a white solid; 1H NMR (400 MHz, CD3OD) δ 3.24 (t, J=17.4, 8.7 Hz, 2H), 4.55 (t, J=17.4, 8.7 Hz, 2H), 6.80 (d, J=8.2 Hz, 1H), 7.36 (d, J=8.2 Hz, 1H), 7.50 (s, 1H), 7.58 (s, 1H), 7.98 (s, 2H), 8.24 (s, 1H), 8.38 (s, 1H).

Workup

concentrationThe mixture was concentrated
customto afford a yellow solid
customPurification by preparative LCMS (column LUNA 10μ C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record: ord-7096369a8cba4005928ed00a1d4ddeab
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432375B2

Reaction notes

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