8-Hydroxyquinoline → HCID 54767062, compound

HRID 336116Notes

Reaction equation

HRID 336116 reaction equation
[CH3:1][C:2]1([CH3:27])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:26]=[CH:25][C:12]([CH2:13][O:14][C:15]3[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=3C(OC)=O)=[CH:11][CH:10]=2)[O:3]1.OC1C=CC=C2C=1[N:37]=[CH:36][CH:35]=[CH:34]2.BrCC1C=CC(B2OC(C)(C)C(C)(C)O2)=CC=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:27][C:2]1([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5][B:4]([C:9]2[CH:10]=[CH:11][C:12]([CH2:13][O:14][C:15]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:16]=3[N:37]=[CH:36][CH:35]=[CH:34]4)=[CH:25][CH:26]=2)[O:3]1

Participants

6

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 54767384HCID 54767384, compound

Product 1

HCID 54767062HCID 54767062, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The synthesis of B14 was accomplished following the procedure outlined for B1 using 8-hydroxyquinoline (0.12 g, 0.8 mmol), 4-bromomethylphenyl boronic acid pinacol ester (0.26 g, 0.88 mmol), and K2CO3 (0.33 g, 2.4 mmol) in 10 mL of acetonitrile affording B14 in 22% yield (0.06 g, 0.17 mmol). 1H NMR (400 MHz, CDCl3) δ=8.96 (dd, Jj=4.4 Hz, J2=1.2 Hz, 1H), 8.09 (dd, J1=8.4 Hz, J2=1.6 Hz, 1H), 7.79 (d, J=7.6 Hz, 2H), 7.49 (d, J=7.6 Hz, 2H), 7.40 (dd, J1=8 Hz, J2=4 Hz, 1H) 7.34-7.28 (m, 2H), 6.95 (dd, 7.79 J1=7.2 Hz, J2=1.6 Hz, 1H), 5.47 (s, 2H), 1.31 (s, 12H). 13C NMR (100 MHz, CDCl3) δ=154.38, 149.60, 140.69, 140.42, 136.13, 135.32, 129.70. 126.77, 126.26, 121.84, 120.11, 110.25, 84.01, 70.87, 25.08. ESI-MS(+): m/z 362.02 [M+H]+.

Workup

  1. customThe synthesis of B14

Sources & evidence

ORD record
ord-4983a282733548bfaa80178493205e12
Source dataset
uspto-grants-2014_11
Patent number
US08889638B2

Reaction notes

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