Sodium Carbonate → HCID 89886747, compound

HRID 1403077Notes

Reaction equation

HRID 1403077 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([Br:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:13]([C:15]1[CH:20]=[CH:19][C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][C:16]=1[NH:30][CH:31]1[CH2:36][CH2:35][CH:34]([OH:37])[CH2:33][CH2:32]1)#[N:14].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[Br:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[CH:4][N:3]=[C:2]2[C:18]1[CH:19]=[CH:20][C:15]([C:13]#[N:14])=[C:16]([NH:30][CH:31]2[CH2:36][CH2:35][CH:34]([OH:37])[CH2:33][CH2:32]2)[CH:17]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 211924975-Bromo-1-chloroisoquinolineHCID 1317321714-Cyano-3-(4-hydroxycyclohexylamino)phenylboronic acid pinacol ester

Product 1

HCID 89886747HCID 89886747, compoundYield 153.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Pd(PPh3)4 (1.39 g) was added to a solution of compound (1b) (5.83 g), 4-cyano-3-(4-hydroxycyclohexylamino)phenylboronic acid pinacol ester (7.80 g), and an aqueous sodium carbonate solution (2 M, 40 mL) in ethylene glycol dimethyl ether (80 mL) in a nitrogen atmosphere, and the mixture was stirred at 85° C. for 3 hours. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by neutral silica gel column chromatography (chloroform/methanol) to obtain compound (2a) (14.8 g, yield: 62%) as a white solid.

Workup

  1. customThe reaction solution was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by neutral silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-62919f940b6f4ef6a141445b8ca76331
Source dataset
uspto-grants-2014_12
Patent number
US08912181B2

Reaction notes

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