Cesium carbonate → (R)-{2-[4-(2,6-dimethyl-imidazo[4,5-c]pyridin-3-yl)-piperidin-1-ylmethyl]-indan-5-yl}-carbamic acid tert-butyl ester

HRID 1716604Notes

Reaction equation

[CH3:1][C:2]1[N:11]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:5]2[CH:6]=[N:7][C:8]([CH3:10])=[CH:9][C:4]=2[N:3]=1.[C:18]([O:22][C:23](=[O:36])[NH:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[CH2:30][C@@H:29]([CH2:34]I)[CH2:28]2)([CH3:21])([CH3:20])[CH3:19].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[C:18]([O:22][C:23](=[O:36])[NH:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[CH2:30][C@@H:29]([CH2:34][N:15]1[CH2:16][CH2:17][CH:12]([N:11]3[C:5]4[CH:6]=[N:7][C:8]([CH3:10])=[CH:9][C:4]=4[N:3]=[C:2]3[CH3:1])[CH2:13][CH2:14]1)[CH2:28]2)([CH3:21])([CH3:19])[CH3:20]

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of 2,6-dimethyl-3-piperidin-4-yl-3H-imidazo[4,5-c]pyridine (20 mg, 0.086 mmol) in acetonitrile (0.80 mL) was treated with (R)-(2-iodomethyl-indan-5-yl)-carbamic acid tert-butyl ester (50 mg, 0.13 mmol) and cesium carbonate (85 mg, 0.26 mmol). The mixture was stirred at 85° C. for 4 hrs. The mixture was filtered and the solvent was evaporated. Flash chromatography (10/1 CH2Cl2/CH3OH) afforded (R)-{2-[4-(2,6-dimethyl-imidazo[4,5-c]pyridin-3-yl)-piperidin-1-ylmethyl]-indan-5-yl}-carbamic acid tert-butyl ester (22 mg, 54%) as a light yellow solid.

Workup

filtrationThe mixture was filtered
customthe solvent was evaporated

Sources & evidence

ORD record: ord-130e2f3848754323aa7df143d9d55f1c
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803816B2

Reaction notes

Loading…