HCID 58269139, compound → HCID 136073762, compound

HRID 1476225Notes

Reaction equation

HRID 1476225 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:20]([C:22]3[O:23][C:24]4[C:29]([C:30](=[O:39])[C:31]=3[C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=3)=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH3:21])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=3[O:18]C)[C:3]=12>ClCCl.B(Br)(Br)Br>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:20]([C:22]3[O:23][C:24]4[C:29]([C:30](=[O:39])[C:31]=3[C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=3)=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH3:21])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=3[OH:18])[C:3]=12

Participants

4

Reactant 1

HCID 58269139HCID 58269139, compound

Product 1

HCID 136073762HCID 136073762, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25134Boron tribromideSolvent

Procedure

To a solution of Example 90 (0.080 g, 0.152 mmoles) in dichloromethane (4 ml), BBr3 (1M in dichloromethane, 0.8 ml) was added at 0° C. and the reaction mixture was warmed to RT and then stirred for 12 h. The reaction mixture was quenched with 1.5N HCl solution and extracted with dichloromethane. The organic layer was dried over sodium sulphate and concentrated. The crude product was purified by column chromatography with methanol: dichloromethane to afford the title compound as off-white solid (0.027 g, 35% yield). MP: 235-237° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 10.66(s,1H), 8.04(d, J=9.8 Hz, 1H), 8.02(s,1H),7.84(t, J=7.0Hz,1H), 7.66(d, J=8.3Hz, 1H), 7.52(t, J=7.9Hz, 1H), 7.35(t, J=7.2Hz, 2H), 7.10(t, J=8.4 Hz, 1H), 6.96(br s,2H), 6.79(m, 2H), 5.98(q, J=7.0 Hz, 1H),1.88(d, J=7.1Hz, 3H). Mass: 512.22(M++1).

Workup

  1. customThe reaction mixture was quenched with 1.5N HCl solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography with methanol

Sources & evidence

ORD record
ord-710e8f3bad9d49a1a0ed14f7aae29deb
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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