HCID 58269214, compound → HCID 136073764, compound

HRID 1476253Notes

Reaction equation

HRID 1476253 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:21][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][C:27]([F:40])=[CH:26][CH:25]=4)[N:9]=[C:10]([C:11]3[CH:16]=[C:15]([F:17])[C:14]([O:18]C)=[C:13]([F:20])[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]([CH2:21][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][C:27]([F:40])=[CH:26][CH:25]=4)[N:9]=[C:10]([C:11]3[CH:12]=[C:13]([F:20])[C:14]([OH:18])=[C:15]([F:17])[CH:16]=3)[C:3]=12

Participants

4

Reactant 1

HCID 58269214HCID 58269214, compound

Product 1

HCID 136073764HCID 136073764, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25134Boron tribromideSolvent

Procedure

To a solution of example 127 (0.099 g, 0.180 mmoles) in dichloromethane (10 ml), BBr3 (1M in dichloromethane, 0.99 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 to afford the title compound as brown solid (0.022 g, 23% yield). MP: 274-278° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 10.20(s, 1H), δ 8.18(s, 1H), 7.72-7.60(m, 4H), 7.38(m, 1H), 7.20 (d, J=8.7 Hz, 2H), 7.17-7.10(m, 4H), 5.51(s, 2H). Mass: 534.06(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

Sources & evidence

ORD record
ord-43a551c37d174660a5021c0581f409bd
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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