Triphenylphosphine → 3-Bromo-1-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]-1h-pyrrolo[2,3-c]pyridine

HRID 272766Notes

Reaction equation

HRID 272766 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[CH3:11][C:12]1([CH3:21])[O:16][CH:15]([CH2:17][CH2:18]CO)[CH2:14][O:13]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1>C1COCC1>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[N:4]([CH2:18][CH2:17][CH:15]2[CH2:14][O:13][C:12]([CH3:21])([CH3:11])[O:16]2)[CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2315513-(2,2-Dimethyl-1,3-dioxolan-4-yl)propan-1-olHCID 5387121Dibenzyl azodicarboxylateHCID 124108563-Bromo-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 692199063-Bromo-1-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]-1h-pyrrolo[2,3-c]pyridineYield 199.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 695J (118 mg, 0.6 mmol), 3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-1-ol (131.6 mg, 0.9 mmol), polymer-supported PPh3 (400 mg, 1.2 mmol), and DBAD (0.268 mg, 1.2 mmol) in THF (3 mL) was stirred at room temperature for 8 hours. The reaction mixture was loaded onto the silica gel column and eluted with 100% EtOActo give 0.39 g of the desired product (67%). MS (DCI) m/e 326 (M+H)+, 1H NMR (500 MHz, DMSO-d6): □ 8.94 (s, 1H), 8.23 (d, J=5.49 Hz, 1H), 7.88 (s, 1H), 7.41 (d, J=5.49 Hz, 1H), 4.37-4.40 (m, 2H), 3.91-3.97 (m, 2H), 3.47 (dd, J=7.63, 6.41 Hz, 1H), 2.07 (m, 1H), 1.98 (m, 1H), 1.34 (s, 3H), 1.24 (s, 3H).

Workup

  1. washeluted with 100%

Sources & evidence

ORD record
ord-1405895a320b432faf4faa44131fb33e
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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