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Formic Acid → 3-(2-methoxy-phenyl)-5-morpholin-4-yl-1H-pyrrolo[2,3-b]pyridine

HRID 729823
Notes
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Reaction equation

HRID 729823 reaction equation
COCCOC[N:7]1[C:11]2=[N:12][CH:13]=[C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH:15]=[C:10]2[C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH3:29])=[CH:8]1.C(O)=O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(O)C.O.[Cl-].[Na+].O>[CH3:29][O:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:9]1[C:10]2[C:11](=[N:12][CH:13]=[C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH:15]=2)[NH:7][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 284Formic AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 59699905HCID 59699905, compound

Product 1

HCID 596998613-(2-methoxy-phenyl)-5-morpholin-4-yl-1H-pyrrolo[2,3-b]pyridineYield 94%

Reagents, catalysts & solvents 3

HCID 702
Ethanol
Solvent
HCID 962WaterSolvent2×
HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
65 °C

Procedure

65 mg (0.17 mmol) of 1-(2-methoxy-ethoxymethyl)-3-(2-methoxy-phenyl)-5-morpholin-4-yl-1H-pyrrolo[2,3-b]pyridine was dissolved in a mixture of 3 ml of ethanol and 2 ml of water. 500 μl of formic acid was added and the mixture heated to 65° C. for 16 h and then irradiated in the microwave to 150° C. for 40 min. The resulting mixture was neutralized by addition of sodium bicarbonate and water and the crude distributed between ethyl acetate and brine. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated to afford 47 mg (0.15 mmol, 94% yield) of 3-(2-methoxy-phenyl)-5-morpholin-4-yl-1H-pyrrolo[2,3-b]pyridine. 1H-NMR (d6-DMSO): δ 11.58 (s, 1H), 8.11 (d, J=2.5 Hz, 1H), 7.59 (d, J=2.4 Hz, 1H), 7.51 (dd, J=1.4 Hz, 7.3 Hz, 1H), 7.46 (s, 1H), 7.27 (ddd, J=1.5 Hz, 8.8 Hz, 1H), 7.11 (d, J=8.3 Hz, 1H), 7.02 (dd(d), J=1.5 Hz, 7.3 Hz, 1H), 3.82 (s, 3H), 3.77 (m, 4H), 3.07 (m, 4H); MS: m/z 310 [MH+].

Workup

  1. customirradiated in the microwave to 150° C. for 40 min
  2. extractionThe aqueous phase was extracted twice with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-07aa6200ed4541e2954dd184db1469a0
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07582637B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes