HCID 58269236, compound → HCID 58269217, compound

HRID 1476200Notes

Reaction equation

HRID 1476200 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:19][C:20]3[O:21][C:22]4[C:27]([C:28](=[O:37])[C:29]=3[C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17]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]([CH2:19][C:20]3[O:21][C:22]4[C:27]([C:28](=[O:37])[C:29]=3[C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=3)[C:3]=12

Participants

4

Reactant 1

HCID 58269236HCID 58269236, compound

Product 1

HCID 58269217HCID 58269217, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25134Boron tribromideSolvent

Procedure

To a solution of example 54 (0.200 g, 0.383 mmoles) in dichloromethane (30 ml), BBr3 (1M in dichloromethane, 2.0 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 off-white solid (0.070 g, 36% yield). MP: 280-283° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 9.69(s,1H), 8.20(s,1H), 8.06(dd, J=8.2,1.7 Hz, 1H), 7.80(m,1H), 7.51(m 2H), 7.39(m,2H), 7.17(m, 2H), 7.11(dt, J=8.7,2.2 Hz, 1H), 7.02(d, J=8.6 Hz, 1H), 7.00(s,1H), 6.86 (dd, J=7.7,1.8Hz, 1H), 5.5 (s, 2H). Mass: 479.88(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-d453e066f726478185ebc2c7a1108f52
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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