Sodium Iodide → 2-{4-[3-(2-Methylpyrrolidin-1-yl)propoxy]phenyl}-1,3-thiazole

HRID 1710779Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[CH:8][CH:7]=1.[I-].[Na+].[CH3:19][CH:20]1[CH2:24][CH2:23][CH2:22][NH:21]1>C(#N)C>[CH3:19][CH:20]1[CH2:24][CH2:23][CH2:22][N:21]1[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of 2-[4-(3-chloropropoxy)phenyl]-1,3-thiazole i88 (120 mg, 1 eq, 0.47 mmol) in acetonitrile (1 ml) is added to a solution of sodium iodide (10 mg, 0.1 eq, 0.07 mmol) and 2-methylpyrrolidine (0.1 ml, 2 eq, 0.9 mmol) in acetonitrile (1 ml). The mixture is stirred at 85° C. overnight, filtered, washed with acetonitrile, and concentrated under reduced pressure. Purification of the residue by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 96/4/0.4) affords 40 mg of 2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-1,3-thiazole 83.

Workup

filtrationfiltered
washwashed with acetonitrile
concentrationconcentrated under reduced pressure
customPurification of the residue by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 96/4/0.4)

Sources & evidence

ORD record: ord-b1aa4db090854b148acc69aeba80cefc
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790720B2

Reaction notes

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