Potassium Carbonate → HCID 58405090, compound

HRID 237269Notes

Reaction equation

HRID 237269 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[OH:20])[CH2:9]1)=O)(C)(C)C.Br[CH:22]1[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([F:31])[CH:28]=2)[C:23]1=O.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:19][C:17]1[CH:16]=[CH:15][C:14]([O:20][CH:22]2[CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[C:27]([F:31])[CH:28]=3)[CH2:23]2)=[C:13]([CH:18]=1)[O:12][CH:10]1[CH2:9][NH:8][CH2:11]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 110316412-Bromo-5-fluoro-1-indanoneHCID 673429093-(5-Chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58405090HCID 58405090, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture of 3-(5-chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (0.5 mmol), the title compound of Step A (0.5 mmol), and K2CO3 (1 mmol) in acetonitrile (3 mL) was heated at 100° C. in a microwave reactor for 1 h. The mixture was cooled to rt and purified via PTLC providing the title compound (150 mg). To this product was added DCE (5 mL), Et3SiH (1 mL) and TFA (3 mL). The mixture was stirred at 80° C. for 16 h. After concentration, the title compound was obtained (91 mg). MS (ESI): mass calcd. for C18H17ClFNO2, 333.1; m/z found, 334.1 [M+H]+. 1H NMR (CDCl3): 7.20-7.13 (m, 1H), 6.96-6.60 (m, 5H), 5.18-5.08 (m, 1H), 4.93-4.83 (m, 1H), 3.98-3.70 (m, 4H), 3.38-3.05 (m, 4H).

Workup

  1. custompurified via PTLC

Sources & evidence

ORD record
ord-c11e04f8eaa44c13ae18b6a73c6b8fd0
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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