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tert-Butanol → 1H-Pyrrolo[2,3-b]pyridine-4-carboxylic acid,1,1-dimethylethyl ester

HRID 549077
Notes
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Reaction equation

HRID 549077 reaction equation
[NH:1]1[C:5]2[N:6]=[CH:7][CH:8]=[C:9]([C:10]([OH:12])=[O:11])[C:4]=2[CH:3]=[CH:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:25](O)([CH3:28])([CH3:27])[CH3:26].C1CCN2C(=NCCC2)CC1>CN(C)C=O>[NH:1]1[C:5]2[N:6]=[CH:7][CH:8]=[C:9]([C:10]([O:12][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:11])[C:4]=2[CH:3]=[CH:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 224774261H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

Product 1

HCID 730136421H-Pyrrolo[2,3-b]pyridine-4-carboxylic acid,1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A stirred suspension of 1H-pyrrolo[2,3-b]pyridine-4 carboxylic acid (0.2 g, reference Example 69) in dry dimethylformamide (5 mL), under nitrogen, was treated with 1,1′-carbonyldiimidazole (0.2 g). After stirring at room temperature for 1 hour the resulting tan coloured solution was treated with tert-butanol (260 μL) and DBU (203 μL). This mixture was stirred at 40° C. overnight then evaporated. The residue was partitioned between water (30 mL) and ethyl acetate (30 mL) and the aqueous layer was then extracted twice with ethyl acetate (10 mL). The combined organics were washed twice with brine (10 mL), then dried over sodium sulfate and then evaporated to give the title compound (0.21 g) as a yellow solid.

Workup

  1. stirringThis mixture was stirred at 40° C. overnight
  2. customthen evaporated
  3. customThe residue was partitioned between water (30 mL) and ethyl acetate (30 mL)
  4. extractionthe aqueous layer was then extracted twice with ethyl acetate (10 mL)
  5. washThe combined organics were washed twice with brine (10 mL)
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-39aec45b0088419cab6077b27c8407a0
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07943616B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes