tert-Butanol → HCID 71087194, compound

HRID 1478898Notes

Reaction equation

HRID 1478898 reaction equation
[CH2:1]([N:3]1[C:11]2[CH:10]=[C:9](C(O)=O)[N:8]=[CH:7][C:6]=2[C:5]([CH3:15])=[CH:4]1)[CH3:2].C1(P([N:30]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:33][C:34]([OH:37])([CH3:36])[CH3:35].C1[CH2:42][O:41]CC1>>[CH2:1]([N:3]1[C:11]2[CH:10]=[C:9]([NH:30][C:42](=[O:41])[O:37][C:34]([CH3:36])([CH3:35])[CH3:33])[N:8]=[CH:7][C:6]=2[C:5]([CH3:15])=[CH:4]1)[CH3:2]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8028Tetrahydrofuran2×HCID 199401P,P-Diphenylphosphinic azideHCID 71087699HCID 71087699, compound

Product 1

HCID 71087194HCID 71087194, compoundYield 38%

Conditions

Temperature
85 °C

Procedure

In a 50 ml sealed cap glass vessel, 1-ethyl-3-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (1O, 1.75 g, 8.57 mmol), Diphenylphosphoryl azide (2.408 ml, 11.14 mmol), and TEA (2.389 ml, 17.14 mmol) were dissolved in THF (Ratio: 1.000, Volume: 6.00 ml) and added t-BuOH (Ratio: 1.000, Volume: 6 ml) and sealed the cap and heated on oil bath at 85° C. for 2 hrs. Then transferred into round bottom flask using THF, evaporated the reaction mixture and purified using column chromatography (Hexane-Ethyl acetate mixtures). Pure product fractions were collected and concentrated to obtain the product tert-butyl 1-ethyl-3-methyl-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (1P, 0.9 g, 38% yield) as a fluffy white solid. 1 H NMR (400 MHz, DMSO-d6) δ ppm 1.32 (t, J=7.20 Hz, 3 H) 1.49 (s, 9 H) 2.26 (d, J=1.26 Hz, 3 H) 4.06 (q, J=7.24 Hz, 2 H) 7.10 (d, J=1.01 Hz, 1H) 7.73 (s, 1 H) 8.33-8.51 (m, 1 H) 9.49 (br. s., 1 H).

Workup

  1. customIn a 50 ml sealed
  2. customcap glass vessel
  3. customsealed the
  4. customcap
  5. customThen transferred into round bottom flask
  6. customevaporated the reaction mixture
  7. custompurified
  8. customPure product fractions were collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-7490286d5a384cf6b495419619860403
Source dataset
uspto-grants-2016_08
Patent number
US09403819B2

Reaction notes

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