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Cesium carbonate → methyl 4-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 1912545
Notes
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Reaction equation

HRID 1912545 reaction equation
[NH2:1][C:2]1[C:11]([CH:12]=O)=[C:10]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[O:20][CH2:19][CH2:18][CH2:17]3)[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:24])[N:3]=1.[C:25](=O)([O-])[O-].[Cs+].[Cs+].[Si](C=[N+]=[N-])(C)(C)C>CO>[O:20]1[C:21]2[C:16](=[CH:15][C:14]([C:10]3[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:24])[N:3]=[C:2]4[NH:1][CH:25]=[CH:12][C:11]=34)=[CH:23][CH:22]=2)[CH2:17][CH2:18][CH2:19]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 167693TrimethylsilyldiazomethaneHCID 86675740Methyl 6-amino-4-(chroman-6-yl)-5-formyl-2-methylnicotinate

Product 1

HCID 71209166methyl 4-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 887Methanol
Solvent

Conditions

Temperature
55 °C

Procedure

A mixture of methyl 6-amino-4-(chroman-6-yl)-5-formyl-2-methylnicotinate (4.5 g, 13.79 mmol) and cesium carbonate (8.99 g, 27.6 mmol) in methanol (180 mL) was heated to 55° C. and then treated with TMSCHN2, 2.0 M solution in hexanes (27.6 mL, 55.2 mmol). The mixture was heated to 60° C. for several minutes until LCMS and TLC showed the reaction was complete. The mixture was cooled in an ice-bath and then quenched with saturated ammonium chloride. The mixture was extracted with ethyl acetate. The extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to afford the crude product (4.3 g, 13.34 mmol, 97% yield) as a pale yellow solid: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.34 (br. s., 1 H), 7.28-7.21 (m, 2 H), 6.93-6.87 (m, 1 H), 6.48 (d, J=2.9 Hz, 1 H), 4.30-4.25 (m, 2 H), 3.72-3.68 (m, 3 H), 2.90-2.83 (m, 2 H), 2.74 (s, 3 H), 2.12-2.05 (m, 2 H); LC/MS (m/z) ES+=323.24 (M+1).

Workup

  1. temperatureThe mixture was heated to 60° C. for several minutes until LCMS and TLC
  2. temperatureThe mixture was cooled in an ice-bath
  3. customquenched with saturated ammonium chloride
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f0dc20f497ba4faaa1258943a3315b6a
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08609653B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes