HCID 58269137, compound → HCID 58269195, compound

HRID 1476231Notes

Reaction equation

HRID 1476231 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]=[CH:13][C:12]=3[Cl:19])[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]=[CH:13][C:12]=3[Cl:19])[C:3]=12

Participants

4

Reactant 1

HCID 58269137HCID 58269137, compound

Product 1

HCID 58269195HCID 58269195, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25134Boron tribromideSolvent

Procedure

To a solution of Example 96 (0.030 g, 0.055 mmoles) in dichloromethane (3 ml), BBr3 (1M in dichloromethane, 0.27 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 pale green solid (0.018 g, 62% yield). MP: 192-195° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 9.95(s,1H),8.15(s,1H), 8.05(dd, J=7.9,1.2Hz, 1H), 7.86(m, 1H), 7.65-7.49(m,4H), 7.39(d, J=8.7Hz, 1H), 7.35(br s,1H), 7.11(t, J=7.5Hz, 1H), 6.97(dd, J=7.6,3.2Hz, 1H), 6.86(d, J=2.8Hz, 1H), 6.07(q, J=6.9 Hz, 1H),1.88(d, J=7.0Hz, 3H). Mass: 527.90(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

Sources & evidence

ORD record
ord-bb5378f9fabe4840aa49e0ec2aa657a8
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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