HCID 58269112, compound → HCID 58269225, compound

HRID 1476250Notes

Reaction equation

HRID 1476250 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:20][C:21]3[O:22][C:23]4[C:28]([C:29](=[O:38])[C:30]=3[C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=3)=[CH:27][C:26]([F:39])=[CH:25][CH:24]=4)[N:9]=[C:10]([C:11]3[CH:16]=[C:15]([O:17]C)[CH:14]=[C:13]([F: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]([CH2:20][C:21]3[O:22][C:23]4[C:28]([C:29](=[O:38])[C:30]=3[C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=3)=[CH:27][C:26]([F:39])=[CH:25][CH:24]=4)[N:9]=[C:10]([C:11]3[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([F:19])[CH:12]=3)[C:3]=12

Participants

4

Reactant 1

HCID 58269112HCID 58269112, compound

Product 1

HCID 58269225HCID 58269225, compoundYield 31.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25134Boron tribromideSolvent

Procedure

To a solution of Example 120 (0.075 g, 0.140 mmoles) in dichloromethane (10 ml), BBr3 (1M in dichloromethane, 1.0 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 light brown solid (0.023 g, 31% yield). MP: 127-129° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 10.18(s,1H), 8.19(s, 1H), 7.74-7.61(m, 3H), 7.38(q, J=7.8 Hz, 1H),7.15(m,3H), 6.84(s,1H), 6.81(d, J=8.8 Hz, 1H), 6.65(d, J=10.8 Hz, 1H), 5.54(s, 2H). Mass: 515.54(M+).

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-dbf65a732ea34f3e93a9f76192a2eee6
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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