Hexane → HCID 11575798, compound

HRID 735256Notes

Reaction equation

HRID 735256 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:10]2([CH3:24])[C:19](=[O:20])[C:18]3[C:13](=[C:14]([Br:22])[CH:15]=[C:16]([Br:21])[CH:17]=3)[NH:12][C:11]2=[O:23])[CH:5]=[CH:6][C:7]=1[O:8]C.B(Br)(Br)Br.CCCCCC>CCOC(C)=O>[NH2:1][C:2]1[CH:3]=[C:4]([C:10]2([CH3:24])[C:19](=[O:20])[C:18]3[C:13](=[C:14]([Br:22])[CH:15]=[C:16]([Br:21])[CH:17]=3)[NH:12][C:11]2=[O:23])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 8058HexaneHCID 25134Boron tribromideHCID 11590559HCID 11590559, compound

Product 1

HCID 11575798HCID 11575798, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The objective compound was prepared by the same procedure for the example 13, using a 3-(3-amino-4-methoxy-phenyl)-6,8-dibromo-3-methyl-1H-quinoline-2,4-dione (36 mg, 0.079 mmol) and BBr3(0.4 mL, 1.0 M solution in dichloromethane). After normal workup, the pure objective compound (18 mg, 52%) was obtained as pale yellow solid by a flash column chromatography (n-hexane:EtOAc=3:1): 1H NMR (200 MHz, CDCl3) δ 1.64 (s, 3H, CH3), 4.85 (br s, 3H, NH2 & OH), 6.41 (d, J=2.4 Hz, 1H, ArH), 6.37 (dd, J=8.6, 2.4 Hz, 1H, ArH), 6.55-6.61 (m, 2H, ArH), 7.86 (d, J=2.0 Hz, 1H, ArH); HRMS m/e cacld. for C16H12N2O3Br2 437.9215, found 437.9211.

Workup

  1. customThe objective compound was prepared by the same procedure for the example 13

Sources & evidence

ORD record
ord-4c75b67615814c68bc77fe5e2919c440
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

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