Dichloromethane → 5-Morpholin-4-yl-3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 2114073Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 57 (0.031 g, 0.076 mmol) and 10% aqueous NaOH solution (1 mL) in EtOH (2 mL) was stirred at 90° C. for 1 hour. The mixture was cooled and evaporated to afford a tan syrup. The syrup was dissolved with CH2Cl2 and the solution was washed with brine. The aqueous layer was extracted twice with CH2Cl2. The combined extracts were dried (MgSO4) and concentrated to afford a syrup, which was purified by means of preparative TLC with CH2Cl2:MeOH as eluent to afford 58 (0.016 g, 78%) as a pale brown solid. 1H NMR (400 MHz, CD3OD) δ 3.13-3.17 (m, 4H), 3.85-3.89 (m, 4H), 7.51 (s, 1H), 7.74 (d, J=0.26 Hz, 1H), 7.93 (bs, 2H), 8.06 (d, J=0.26 Hz, 1H).

Workup

temperatureThe mixture was cooled
customevaporated
customto afford a tan syrup
washthe solution was washed with brine
extractionThe aqueous layer was extracted twice with CH2Cl2
dry with materialThe combined extracts were dried (MgSO4)
concentrationconcentrated
customto afford a syrup, which
customwas purified by means of preparative TLC with CH2Cl2

Sources & evidence

ORD record: ord-9ecd6d82e4ff4caea8f528a1cd565513
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432375B2

Reaction notes

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