HCID 66580147, compound → HCID 136073766, compound

HRID 239671Notes

Reaction equation

HRID 239671 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]=[CH:15][C:14]([O:17]C)=[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]([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]=[CH:15][C:14]([OH:17])=[C:13]([F:19])[CH:12]=3)[C:3]=12

Participants

4

Reactant 1

HCID 66580147HCID 66580147, compound

Product 1

HCID 136073766HCID 136073766, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25134Boron tribromideSolvent

Procedure

To a solution of example 84 (0.100 g, 0.190 mmoles) in dichloromethane (4 ml), BBr3 (1M in dichloromethane, 1 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 pale green solid (0.061 g, 63% yield). MP: 244-247° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 10.19(s,1H), 8.04(s, 1H), 8.04(dd, J=8.0,1.4 Hz, 1H), 7.85(m,1H), 7.68(d, J=8.4 Hz, 1H), 7.52(t, J=7.2 Hz, 1H), 7.33(m,2H), 7.24(dd, J=8.2,1.4 Hz, 1H), 7.09-6.91(m,4H), 6.00(q, J=7.0 Hz, 1H),1.88(d, J=7.0 Hz, 1H). Mass: 511.94(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-37b8d34f3c34462ea87fc76c76e046a7
Source dataset
uspto-grants-2014_02
Patent number
US08642607B2

Reaction notes

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