tert-Butanol → HCID 67354352, compound

HRID 1478897Notes

Reaction equation

HRID 1478897 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[C:8](C(O)=O)[N:7]=[CH:6][C:5]=2[C:4]([CH3:14])=[CH:3]1.C1(P([N:29]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:32][C:33]([OH:36])([CH3:35])[CH3:34].C1[CH2:41][O:40]CC1>>[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([NH:29][C:41](=[O:40])[O:36][C:33]([CH3:35])([CH3:34])[CH3:32])[N:7]=[CH:6][C:5]=2[C:4]([CH3:14])=[CH:3]1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8028Tetrahydrofuran2×HCID 199401P,P-Diphenylphosphinic azideHCID 67355216HCID 67355216, compound

Product 1

HCID 67354352HCID 67354352, compoundYield 56%

Conditions

Temperature
85 °C

Procedure

In a 100 ml sealed cap glass pressure vessel, 1,3-dimethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (1K, 1.7 g, 9.0 mmol), diphenylphosphoryl azide (2.1 ml, 9.8 mmol), and TEA (2.5 ml, 18 mmol) were dissolved in THF (10 ml). To this mixture was added t-BuOH (10 ml) and with the cap sealed, the mixture was heated in an oil bath at 85° C. for 4 hrs. After cooling the mixture was transferred into a round bottom flask using THF, concentrated in vacuo and purified using column chromatography (hexanes-ethyl acetate (0-100%)). Pure product fractions were collected and solvents were evaporated to obtain the product tert-butyl 1,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (1L, 1.3 g, 56%) as a fluffy white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.49 (s, 9 H) 2.25 (d, J=1.01 Hz, 3 H) 3.66 (s, 3 H) 7.02 (d, J=1.01 Hz, 1 H) 7.59-7.78 (m, 1 H) 8.43 (d, J=1.01 Hz, 1 H) 9.40 (s, 1 H).

Workup

  1. customIn a 100 ml sealed
  2. customcap glass pressure vessel
  3. customwith the cap sealed
  4. temperatureAfter cooling the mixture
  5. customwas transferred into a round bottom flask
  6. concentrationconcentrated in vacuo
  7. custompurified
  8. customPure product fractions were collected
  9. customsolvents were evaporated

Sources & evidence

ORD record
ord-5276f42b999b4f9c94c6ce9b1cf7b870
Source dataset
uspto-grants-2016_08
Patent number
US09403819B2

Reaction notes

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