tert-Butanol → HCID 71087194, compound

HRID 2405085Notes

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

Reactant 4

HCID 6386tert-Butanol

HCID 8028Tetrahydrofuran2×

HCID 199401P,P-Diphenylphosphinic azide

HCID 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. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.32 (t, J=7.20 Hz, 3H) 1.49 (s, 9H) 2.26 (d, J=1.26 Hz, 3H) 4.06 (q, J=7.24 Hz, 2H) 7.10 (d, J=1.01 Hz, 1H) 7.73 (s, 1H) 8.33-8.51 (m, 1H) 9.49 (br. s., 1H).

Workup

customIn a 50 ml sealed
customcap glass vessel
customsealed the
customcap
customThen transferred into round bottom flask
customevaporated the reaction mixture
custompurified
customPure product fractions were collected
concentrationconcentrated

Sources & evidence

ORD record: ord-539fa6b2acac4e339eac2b025e55fae7
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802695B2

Reaction notes

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