Deferiprone → HCID 54767212, compound

HRID 336115Notes

Reaction equation

HRID 336115 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]OC3C=CC=CC=3C(OC)=O)=[CH:11][CH:10]=2)[O:3]1.[OH:28][C:29]1[C:34](=[O:35])[CH:33]=[CH:32][N:31]([CH3:36])[C:30]=1[CH3:37].BrCC1C=CC(B2OC(C)(C)C(C)(C)O2)=CC=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:36][N:31]1[CH:32]=[CH:33][C:34](=[O:35])[C:29]([O:28][CH2:13][C:12]2[CH:11]=[CH:10][C:9]([B:4]3[O:3][C:2]([CH3:27])([CH3:1])[C:6]([CH3:8])([CH3:7])[O:5]3)=[CH:26][CH:25]=2)=[C:30]1[CH3:37]

Participants

6

Reactant 4

HCID 2972DeferiproneHCID 11430Potassium CarbonateHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 54767384HCID 54767384, compound

Product 1

HCID 54767212HCID 54767212, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The synthesis of B12 was accomplished following the procedure outlined for B1 using 3-hydroxy-1,2-dimethylpyridin-4(1H)-one (80 mg, 0.54 mmol), 4-bromomethylphenyl boronic acid pinacol ester (180 mg, 0.59 mmol), and K2CO3(223 mg, 1.6 mmol) in 8 mL of acetonitrile affording B12 in 50% yield (0.09 g, 0.26 mmol). 1HNMR (400 MHz, CDCl3) δ=7.70 (d, J=8.4 Hz, 2H), 7.36 (d, J=8.4 Hz, 2H), 7.11 (d, J=7.6 Hz, 1H), 6.27 (d, J=7.6 Hz, 1H), 5.18 (s, 2H), 3.44 (s, 3H), 2.02 (s, 3H), 1.29 (s, 12H). 13C NMR (100 MHz, CDCl3) δ=173.55, 146.13, 141.63, 140.83, 139.19, 134.91, 128.46, 117.21, 84.05, 73.00, 41.80, 24.97, 13.15. ESI-MS(+): m/z 356.20 [M+H]+, 378.10 [M+Na]+.

Workup

  1. customThe synthesis of B12

Sources & evidence

ORD record
ord-5264d8cecef24e3da0b50740b7c4d1cf
Source dataset
uspto-grants-2014_11
Patent number
US08889638B2

Reaction notes

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