Potassium Carbonate → HCID 58816576, compound

HRID 2354081Notes

Reaction equation

HRID 2354081 reaction equation
[CH2:1]([C:8]1([OH:27])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][NH:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22](Cl)[CH:21]=2)=[O:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B1([CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)C2CCCC1CCC2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>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(COC)OC>[CH2:1]([C:8]1([OH:27])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][NH:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:21]=2)=[O:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 41509249-Benzyl-9-borabicyclo(3.3.1)nonaneHCID 86610992HCID 86610992, compound

Product 1

HCID 58816576HCID 58816576, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-[2-(4-benzyl-4-hydroxy-piperidin-1-yl)-ethyl]-3-(2-chloro-pyridin-4-yl)-urea (98 mg, 0.3 mmol), B-benzyl-9-BBN (0.5 M in THF, 4 mL, 2 mmol), triphenylphosphine (29 mg, 0.11 mmol), tetrakis(triphenylphosphine)palladium(0) (11 mg, 0.01 mmol), 2 M aq. K2CO3 (0.5 mL) and dimethoxyethane (1 mL) is degassed and heated under argon at 90° C. for 7 days. The mixture is evaporated and the residue purified by preparative HPLC to provide the title compound.

Workup

  1. customis degassed
  2. customThe mixture is evaporated
  3. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-5e5baf38907c4255930ce6b029406d28
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

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