Cesium carbonate → 4-[4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-piperidine-1-carboxylic Acid Tert-Butyl Ester

HRID 8242Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([OH:25])=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1.[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36](Br)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([O:25][C:21]2[CH:20]=[C:19]3[C:24]([C:15]([C:8]4[C:7]([C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=5)=[N:11][N:10]5[CH2:12][CH2:13][CH2:14][C:9]=45)=[CH:16][CH:17]=[N:18]3)=[CH:23][CH:22]=2)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ol (0.27 g, 0.84 mmol) in N,N-dimethylformamide (15 mL) is added 4-bromo-piperidine-1-carboxylic acid tert-butyl ester (0.29 mL, 2.28 mmol) and cesium carbonate (1.5 g, 4.57 mmol). The mixture is heated at 80° C. for 48 h and concentrated in vacuo. The residue is taken up in dichloromethane, washed with water and saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated in vacuo. The residue is chromatographed on SiO2 (7% methanol in dichloromethane) to yield the title compound, 262 mg (61%), as a yellow oil.

Workup

concentrationconcentrated in vacuo
washwashed with water and saturated aqueous sodium chloride
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue is chromatographed on SiO2 (7% methanol in dichloromethane)

Sources & evidence

ORD record: ord-c500204820b146478e6852cd150b3ce0
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087626B2

Reaction notes

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