HCID 58269163, compound → HCID 136073773, compound

HRID 1476224Notes

Reaction equation

HRID 1476224 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:38])[C:30]=3[C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[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][C:14]([O:17]C)=[CH:13][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:38])[C:30]=3[C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=3)=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH3:20])[N:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=3)[C:3]=12

Participants

4

Reactant 1

HCID 58269163HCID 58269163, compound

Product 1

HCID 136073773HCID 136073773, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25134Boron tribromideSolvent

Procedure

To a solution of Example 88 (0.150 g, 0.295 mmoles) in dichloromethane (4 ml), BBr3 (1M in dichloromethane, 1.5 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 off-white solid (0.048 g, 33% yield). MP: 244-247° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 9.79(s,1H), 8.04(s, 1H), 8.04(dd, J=8.5,1.4 Hz, 1H), 7.85(m,1H), 7.68(d, J=8.5Hz, 1H), 7.53(t, J=7.6Hz, 1H), 7.42(d, J=8.5Hz, 2H), 7.28(br s,1H), 7.06(t, J=8.5 Hz, 1H), 6.91(d, J=8.5Hz, 2H), 6.91(br s,2H), 6.00(q, J=7.1 Hz, 1H),1.88(d, J=7.0 Hz, 3H). Mass: 492.69(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
  5. customThe crude product was purified by column chromatography with methanol

Sources & evidence

ORD record
ord-37a925629f1b437ba2c4348d1726fe4d
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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