HCID 58269137, compound → HCID 58269195, compound

HRID 239680Notes

Reaction equation

HRID 239680 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=7.9,1.2 Hz, 1H), 7.86(m, 1H), 7.65-7.49(m,4H), 7.39(d, J=8.7 Hz, 1H), 7.35(br s,1H), 7.11(t, J=7.5 Hz, 1H), 6.97(dd, J=7.6,3.2 Hz, 1H), 6.86(d, J=2.8 Hz, 1H), 6.07(q, J=6.9 Hz, 1H),1.88(d, J=7.0 Hz, 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-d3faf925cf29418eba07638a235c9af0
Source dataset
uspto-grants-2014_02
Patent number
US08642607B2

Reaction notes

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