2-Aminophenylboronic acid hydrochloride → HCID 11965289, compound

HRID 1984512Notes

Reaction equation

HRID 1984512 reaction equation
Br[C:2]1[C:3]([C:16]#[N:17])=[N:4][N:5]([CH2:13][CH2:14][CH3:15])[C:6]=1[CH2:7][C:8]([C:11]#[N:12])([CH3:10])[CH3:9].Cl.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O>>[NH2:17][C:16]1[C:3]2=[N:4][N:5]([CH2:13][CH2:14][CH3:15])[C:6]([CH2:7][C:8]([CH3:9])([CH3:10])[C:11]#[N:12])=[C:2]2[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=1

Participants

3

Reactant 2

HCID 164270902-Aminophenylboronic acid hydrochlorideHCID 66958615HCID 66958615, compound

Product 1

HCID 11965289HCID 11965289, compoundYield 54.7%

Procedure

A modification of the method described in Example 1283 was used to couple 4-bromo-5-(2-cyano-2-methylpropyl)-1-propyl-1H-pyrazole-3-carbonitrile (1.48 g, 5.00 mmol) with 2-aminophenylboronic acid hydrochloride (1.73 g, 10.0 mmol). The reaction was completed in one hour. The coupling product was purified by IFC (silica cartridge, eluting with 40% to 60% ethyl acetate in hexane). The reaction with hydrogen chloride was heated at reflux for a total of about seven hours. 3-(4-Amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)-2,2-dimethylpropanenitrile (840 mg) was obtained as a white solid, mp 248-250° C.

Workup

  1. customThe coupling product was purified by IFC (silica cartridge, eluting with 40% to 60% ethyl acetate in hexane)
  2. customThe reaction with hydrogen chloride
  3. temperaturewas heated
  4. temperatureat reflux for a total of about seven hours

Sources & evidence

ORD record
ord-6b56b02944ea4fbd8a1e59d9d82e92da
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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