Sodium Carbonate → 6-Isopropyl-8-[3-(hydroxymethyl)phenyl]quinoline

HRID 2187903Notes

Reaction equation

[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12](Br)[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:3])[CH3:2].[OH:15][CH2:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:16][OH:15])[CH:22]=3)[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-isopropyl-8-Bromoquinoline (11.1 g, 44.4 mmol) (described in International Patent Publication WO 94/22852), 3-(hydroxymethyl)phenylboronic acid (8.70 g, 57.2 mmol), Na2CO3 (2M, 71 mL, 142 mmol) and Pd(PPh3)4 (2.51 mg, 2.17 mmol) in 280 mL of DME was stirred at 80° C. for 5 h. The resulting mixture was cooled to r.t., diluted with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (Hex/EtOAc, 1/1) and stirring in CH2Cl2/hexane (1/9) yielded 6-Isopropyl-8-[3-(hydroxymethyl)phenyl]quinoline as a white solid.

Workup

temperatureThe resulting mixture was cooled to r.t.
washwashed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
stirringFlash chromatography (Hex/EtOAc, 1/1) and stirring in CH2Cl2/hexane (1/9)

Sources & evidence

ORD record: ord-cca822dc7fea4b45b3caf89ad794cb37
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410563B1

Reaction notes

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