HCID 58269136, compound → HCID 136073770, compound

HRID 239701Notes

Reaction equation

HRID 239701 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:21]([C:23]3[O:24][C:25]4[C:30]([C:31](=[O:40])[C:32]=3[C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=3)=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH3:22])[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]([CH:21]([C:23]3[O:24][C:25]4[C:30]([C:31](=[O:40])[C:32]=3[C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=3)=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH3:22])[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 58269136HCID 58269136, compound

Product 1

HCID 136073770HCID 136073770, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25134Boron tribromideSolvent

Procedure

To a solution of example 126 (0.122 g, 0.224 mmoles) in dichloromethane (10 ml), BBr3 (1M in dichloromethane, 1.2 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 (0.086 g, 72% yield). MP: 253-257° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 9.64(s,1H), 8.05(s,1H), 8.04(dd, J=8.0,1.4 Hz, 1H), 7.83(m,1H), 7.68(d, J=8.4 Hz, 1H), 7.52(t, J=5.3 Hz, 1H), 7.30(m,1H), 7.20(d, J=8.7 Hz, 2H), 7.06(dt, J=8.7,2.2 Hz, 1H), 6.98(br s, 2H), 6.00(q, J=7.0 Hz, 1H),1.88(d, J=7.0 Hz, 3H). Mass: 5530.14(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-4e0acc7a528c40e9a9109e475793c79e
Source dataset
uspto-grants-2014_02
Patent number
US08642607B2

Reaction notes

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