Cesium carbonate → HCID 68000648, compound

HRID 336555Notes

Reaction equation

HRID 336555 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:30][CH2:29][C:10]3([CH2:13][CH:12]([NH:14][C:15]([O:17][CH2:18][C:19]4[O:23][N:22]=[C:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:20]=4)=[O:16])[CH2:11]3)[CH2:9]2)=[N:6][CH:7]=1.[F:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl>[F:31][C:32]1[CH:37]=[CH:36][C:35]([C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:30][CH2:29][C:10]4([CH2:11][CH:12]([NH:14][C:15]([O:17][CH2:18][C:19]5[O:23][N:22]=[C:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:20]=5)=[O:16])[CH2:13]4)[CH2:9]3)=[N:6][CH:7]=2)=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2856454-Fluorophenylboronic acidHCID 68000491HCID 68000491, compound

Product 1

HCID 68000648HCID 68000648, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The process is performed according to the procedure described in Example 2 (step 2.7.). Starting with 1.00 g (2.09 mmol) of ethyl 5-[6-(5-bromopyridin-2-yl)-6-azaspiro[3.4]oct-2-ylcarbamoyloxymethyl]isoxazole-3-carboxylate (isomer 6) and 0.29 g (2.09 mmol) of 4-fluorophenylboronic acid, 2.03 g (6.26 mmol) of caesium carbonate and 0.17 g (0.21 mmol) of PdCl2dppf.CH2Cl2, 0.50 g of a gum is obtained after chromatography on silica gel, eluting with a 90/10 mixture of cyclohexane and ethyl acetate.

Sources & evidence

ORD record
ord-db82e54c50ce4b0fbb6964fddc8b3b57
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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