HCID 54760086, compound → HCID 54670047, compound

HRID 449266Notes

Reaction equation

HRID 449266 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[C:13]3[N:15]([CH2:18][C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[N:25]=[CH:24][CH:23]=[CH:22]5)[N:16]=[N:17][C:12]3=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1>ClCCl.B(Br)(Br)Br>[N:25]1[C:26]2[C:21](=[CH:20][C:19]([CH2:18][N:15]3[C:13]4=[N:14][C:9]([C:5]5[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=5)=[CH:10][CH:11]=[C:12]4[N:17]=[N:16]3)=[CH:28][CH:27]=2)[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 54760086HCID 54760086, compound

Product 1

HCID 54670047HCID 54670047, compoundYield 28.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25134Boron tribromideSolvent

Procedure

To a solution of example 2 (0.110 g, 0.299 mmol) in dichloromethane (1 ml), BBr3 (1M in dichloromethane, 0.82 ml) was added at 0° C. and the reaction mixture was warmed to RT and stirred for 1 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 an off-white solid (0.030 g, 28%). M.P.: 255-257° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 9.70 (s, 1H), 8.88 (dd, J=4.1, 2.6 Hz, 1H), 8.62 (d, J=8.7 Hz, 1H), 8.37 (d, J=8.0 Hz, 1H), 8.04 (m, 3H), 7.83 (dd, J=8.7, 1.8 Hz, 1H), 7.64 (s, 1H), 7.64 (d, J=8.6 Hz, 1H), 7.53 (dd, J=8.3, 4.2 Hz, 1H), 7.35 (t, J=7.9 Hz, 1H), 6.92 (dd, J=7.9, 1.4 Hz, 1H), 6.19 (s, 2H). MS (m/z): 354.02 (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-5cc42b3d251f4f998e22936b5d2da47a
Source dataset
uspto-grants-2013_07
Patent number
US08481739B2

Reaction notes

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