HCID 53235003, compound → HCID 53235004, compound

HRID 1484331Notes

Reaction equation

HRID 1484331 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:19]([C:21]3[O:22][C:23]4[C:28]([C:29](=[O:37])[C:30]=3[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH3:20])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17]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:19]([C:21]3[O:22][C:23]4[C:28]([C:29](=[O:37])[C:30]=3[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH3:20])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=3)[C:3]=12

Participants

4

Reactant 1

HCID 53235003HCID 53235003, compound

Product 1

HCID 53235004HCID 53235004, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25134Boron tribromideSolvent

Procedure

To a solution of example 41 (0.130 g, 0.265 mmoles) in dichloromethane (26 ml), BBr3 (1M in dichloromethane, 2.6 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 under reduced pressure to afford the title compound as light yellow solid (0.070 g, 56% yield). MP: 212-216° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 9.78 (s, 1H), 8.24 (d, J=7.5 Hz, 1H), 8.05 (d, J=7.9 Hz, 1H), 7.85 (t, J=8.4 Hz, 1H), 7.65 (d, J=8.6 Hz, 1H), 7.53 (t, J=7.7 Hz, 1H), 7.36-7.02 (m, 9H), 6.90 (d, J=8.2 Hz, 1H), 6.03 (q, J=6.9 Hz, 1H), 1.91 (d, J=7.3 Hz, 3H). Mass: 476.17 (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 under reduced pressure

Sources & evidence

ORD record
ord-87824bb8d9fa4ab8a5af7558b95a9ce6
Source dataset
uspto-grants-2016_08
Patent number
US09421209B2

Reaction notes

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