Potassium Carbonate → 6-(1H-indol-6-yl)quinolin-2-amine

HRID 930245Notes

Reaction equation

HRID 930245 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](B(O)O)[CH:8]=2)[CH:3]=[CH:2]1.Br[C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[C:19]([NH2:24])[CH:18]=[CH:17]2.C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].COCCOC.CCO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[N:20]=[C:19]([NH2:24])[CH:18]=[CH:17]4)[CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27632051H-Indol-6-ylboronic acidHCID 111836666-Bromoquinolin-2-amine

Product 1

HCID 711385046-(1H-indol-6-yl)quinolin-2-amineYield 54.3%

Reagents, catalysts & solvents 2

HCID 15220664Palladium--triphenylphosphane (1/1)CatalystHCID 20074477Dimethoxyethane ethanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 1H-indol-6-ylboronic acid (43 mg, 0.27 mmol), 6-bromoquinolin-2-amine (40 mg, 0.22 mmol), K2CO3 (3M, 100 uL), PS—PPh3-Pd (20 mg, 0.11 mmol/g), and DME/EtOH (50%, 1 mL) was heated in a microwave at 140° C. for 10 min. The resulting slurry was filtered and purified by HPLC (10-60% CH3CN/water modified with 0.1% TFA) to give 6-(1H-indol-6-yl)quinolin-2-amine (31 mg). MS (ESI, pos. ion) m/z: 260 (M+1).

Workup

  1. filtrationThe resulting slurry was filtered
  2. custompurified by HPLC (10-60% CH3CN/water modified with 0.1% TFA)

Sources & evidence

ORD record
ord-5f54d73e965346508ce63198e7630bc5
Source dataset
uspto-grants-2016_03
Patent number
US09296698B2

Reaction notes

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