HCID 58269249, compound → HCID 58269299, compound

HRID 239672Notes

Reaction equation

HRID 239672 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]=[C:15]([O:17]C)[CH:14]=[C:13]([Cl:19])[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]=[C:15]([OH:17])[CH:14]=[C:13]([Cl:19])[CH:12]=3)[C:3]=12

Participants

4

Reactant 1

HCID 58269249HCID 58269249, compound

Product 1

HCID 58269299HCID 58269299, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25134Boron tribromideSolvent

Procedure

To a solution of Example 86 (0.100 g, 0.184 mmoles) in dichloromethane (4 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 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 pale green solid (0.032 g, 33% yield). MP: 122-124° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 10.19(s,1H), 8.06(s, 1H), 8.04(dd, J=7.9,1.5 Hz, 1H), 7.86(m,1H), 7.67(d, J=8.3 Hz, 1H), 7.53(t, J=7.1 Hz, 1H), 7.28(br s,1H), 7.06-6.87(m,6H), 6.03(q, J=6.9 Hz, 1H),1.88(d, J=7.1 Hz, 1H). Mass: 528.11(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-d281600797ca4f619c91358c73223696
Source dataset
uspto-grants-2014_02
Patent number
US08642607B2

Reaction notes

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