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

HRID 513197Notes

Reaction equation

HRID 513197 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[C:15]([O:19][C:20]1[CH:29]=[CH:28][C:23]([O:24][CH2:25][CH2:26]O)=[CH:22][CH:21]=1)([CH3:18])([CH3:17])[CH3:16].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[C:15]([O:19][C:20]1[CH:21]=[CH:22][C:23]([O:24][CH2:25][CH2:26][N:10]2[C:6]3[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=3[CH:8]=[C:9]2[C:11]([O:13][CH3:14])=[O:12])=[CH:28][CH:29]=1)([CH3:17])([CH3:16])[CH3:18]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 26599236methyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylateHCID 712301312-(4-Tert-butoxyphenoxy)ethanol

Product 1

HCID 86720574Methyl 1-[2-(4-tert-butoxyphenoxy)ethyl]-4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylateYield 105%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate (500 mg, 2.374 mmole), 2-(4-tert-butoxyphenoxy)ethanol (624 mg, 2.97 mmole), and PPh3 (778 mg, 2.97 mmole) were combined in toluene (10 mL) at RT. To this was added DIAD (0.58 mL, 2.98 mmole) slowly at RT. After 3 hr the mixture was concentrated. Flash column chromatography (Biotage-SNAP-50 g SiO2, 0-25% EtOAc/hexanes) gave the title compound (1.0 g, 105%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.18 (d, J=6.0 Hz, 1 H); 7.44 (d, J=1.0 Hz, 1 H); 7.43-7.38 (m, 1 H); 6.85-6.81 (m, 2 H); 6.64-6.60 (m, 2 H); 4.92 (t, J=5.0 Hz, 2 H); 4.31 (t, J=5.0 Hz, 2 H); 3.95 (s, 3H); 1.26 (s, 9 H).

Workup

  1. concentrationAfter 3 hr the mixture was concentrated

Sources & evidence

ORD record
ord-5a388207a6814effb0e693245ea5e253
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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