HCID 53234766, compound → HCID 58269289, compound

HRID 1476221Notes

Reaction equation

HRID 1476221 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])=[C:13]([O:18]C)[CH:12]=3)[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])=[C:13]([OH:18])[CH:12]=3)[C:3]=12

Participants

4

Reactant 1

HCID 53234766HCID 53234766, compound

Product 1

HCID 58269289HCID 58269289, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25134Boron tribromideSolvent

Procedure

To a solution of Example 82 (0.075 g, 0.142 mmoles) in dichloromethane (15 ml), BBr3 (1M in dichloromethane, 1 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 Hal 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 pale green solid (0.040 g, 55% yield). MP: 241-244° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 10.15(s,1H), 8.05(s, 1H), 8.05(dd, J=8.6,1.5Hz, 1H), 7.86(m, 1H), 7.68(d, J=8.4Hz, 1H),7.53(t, J=7.4Hz, 1H), 7.28(m,2H), 7.20(dd, J=8.5,1.9 Hz, 1H), 7.05(m,4H),6.04(q, J=7.1Hz, 1H),1.88(d, J=7.1Hz, 3H). Mass: 511.94(M+).

Workup

  1. customThe reaction mixture was quenched with 1.5N Hal 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-f4de49b5e6b141cf88964daa9f7256eb
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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