HCID 66580036, compound → HCID 136073772, compound

HRID 1484366Notes

Reaction equation

HRID 1484366 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]=[CH:15][C:14]([O:17]C)=[C:13]([O:19]C)[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:16]=[CH:15][C:14]([OH:17])=[C:13]([OH:19])[CH:12]=3)[C:3]=12

Participants

4

Reactant 1

HCID 66580036HCID 66580036, compound

Product 1

HCID 136073772HCID 136073772, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25134Boron tribromideSolvent

Procedure

To a solution of example 97 (0.180 g, 0.0.335 mmoles) in dichloromethane (10 ml), BBr3 (1M in dichloromethane, 1.8 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 off-white pale solid (0.040 g, 24% yield). MP: 193-195° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 9.27 (s, 1H), 9.22 (s, 1H), 8.05 (dd, J=7.3, 1.4 Hz, 1H), 8.03 (s, 1H), 7.86 (m, 1H), 7.68 (d, J=8.4 Hz, 1H), 7.53 (t, J=7.7 Hz, 1H), 7.35 (s, 1H), 7.27 (br s, 1H), 7.05-6.86 (m, 5H), 6.02 (q, J=7.0 Hz, 1H), 1.87 (d, J=7.0 Hz, 3H). Mass: 509.84 (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-953d7289225c463cb490f4f833e302ce
Source dataset
uspto-grants-2016_08
Patent number
US09421209B2

Reaction notes

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