Methyl 1-[2-(4-tert-butoxyphenoxy)ethyl]-4-(3-ethoxyphenyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate → Methyl 4-(3-ethoxyphenyl)-1-[2-(4-hydroxyphenoxy)ethyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

HRID 513199Notes

Reaction equation

HRID 513199 reaction equation
C([O:5][C:6]1[CH:36]=[CH:35][C:9]([O:10][CH2:11][CH2:12][N:13]2[C:21]3[CH:20]=[CH:19][N:18]=[C:17]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][CH3:30])[CH:23]=4)[C:16]=3[CH:15]=[C:14]2[C:31]([O:33][CH3:34])=[O:32])=[CH:8][CH:7]=1)(C)(C)C>C(O)(C(F)(F)F)=O>[CH2:29]([O:28][C:24]1[CH:23]=[C:22]([C:17]2[C:16]3[CH:15]=[C:14]([C:31]([O:33][CH3:34])=[O:32])[N:13]([CH2:12][CH2:11][O:10][C:9]4[CH:8]=[CH:7][C:6]([OH:5])=[CH:36][CH:35]=4)[C:21]=3[CH:20]=[CH:19][N:18]=2)[CH:27]=[CH:26][CH:25]=1)[CH3:30]

Participants

3

Reactant 1

HCID 71230449Methyl 1-[2-(4-tert-butoxyphenoxy)ethyl]-4-(3-ethoxyphenyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

Product 1

HCID 71230154Methyl 4-(3-ethoxyphenyl)-1-[2-(4-hydroxyphenoxy)ethyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Methyl 1-[2-(4-tert-butoxyphenoxy)ethyl]-4-(3-ethoxyphenyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate (900 mg, 1.842 mmole) was taken up in TFA (10 mL) at RT. After 3 hr the mixture was concentrated. The residue was taken up in saturated NaHCO3 and extracted with EtOAc (3 x). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (Biotage-SNAP-25 g SiO2, 50% EtOAc/hexanes) gave the title compound (637 mg, 80%) as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 8.49 (d, J=6.0 Hz, 1 H); 7.60 (s, 1 H); 7.52-7.38 (m, 4 H); 7.01 (dd, J=8.2, 2.5 Hz, 1 H); 6.68-6.60 (m, 3 H); 5.72 (s, 1 H); 4.97-4.91 (m, 2 H); 4.33-4.27 (m, 2 H); 4.12 (dd, J=13.9, 7.0 Hz, 2 H); 3.93 (s, 3 H); 1.43 (t, J=7.0 Hz, 3 H).

Workup

  1. concentrationAfter 3 hr the mixture was concentrated
  2. extractionextracted with EtOAc (3 x)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ff28dad447f843728b2e052064e08aac
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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