Sodium Carbonate → HCID 68538250, compound

HRID 1992036Notes

Reaction equation

HRID 1992036 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16](Br)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH3:22][C:23]1([CH3:32])[CH2:28][CH2:27][C:26](B(O)O)=[CH:25][CH2:24]1.[C:33]([O-:36])([O-])=[O:34].[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:11]([O:36][C:33]([C:11]1([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([C:26]3[CH2:27][CH2:28][C:23]([CH3:32])([CH3:22])[CH2:24][CH:25]=3)[CH:15]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:34])([CH3:14])([CH3:12])[CH3:10]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 441195554,4-Dimethylcyclohexen-1-ylboronic acidHCID 56834849tert-Butyl 4-(4-amino-3-bromophenyl)-piperidine-1-carboxylate

Product 1

HCID 68538250HCID 68538250, compoundYield 65.7%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 250 mg (0.704 mmol) 4-(4-amino-3-bromo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (as prepared in Example 61, step (c)) in 6 mL toluene and 3 mL EtOH was treated with 119 mg (0.774 mmol) 4,4-dimethyl-cyclohex-1-enylboronic acid and 2.81 mL (5.63 mmol) 2.0 M Na2CO3. The mixture was degassed via sonication, placed under Ar, treated with 56.9 mg (0.0493 mmol) Pd(PPh3)4, and heated to 85° C. for 27 h and allowed to stand at RT for 36 h. The mixture was diluted with EtOAc (15 mL) and washed with water (1×15 mL). The combined aqueous layers were extracted with EtOAc (15 mL), and the combined organic layers were dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a Varian MegaBond Elut 50-gm column with 10-15% EtOAc-hexane afforded 89.0 mg (33%) of the title compound as a tan solid: Mass spectrum (ESI, m/z): Calcd. for C20H29N2O2, 329.2 (M—C4H9+2H), found 329.2.

Workup

  1. customThe mixture was degassed via sonication
  2. washwashed with water (1×15 mL)
  3. extractionThe combined aqueous layers were extracted with EtOAc (15 mL)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09c14d9b44bc4c1aa99f7bd1c70680d3
Source dataset
uspto-grants-2010_01
Patent number
US07645755B2

Reaction notes

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