Water → 9-(1-bromoethyl)-8-fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene

HRID 1530731Notes

Reaction equation

HRID 1530731 reaction equation
P(Br)(Br)[Br:2].[F:5][C:6]1[C:28]([CH:29](O)[CH3:30])=[CH:27][C:9]2[C:10]3[N:14]([CH2:15][CH2:16][O:17][C:8]=2[CH:7]=1)[CH:13]=[C:12]([C:18]1[N:19]([CH:24]([CH3:26])[CH3:25])[N:20]=[C:21]([CH3:23])[N:22]=1)[N:11]=3.O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:2][CH:29]([C:28]1[C:6]([F:5])=[CH:7][C:8]2[O:17][CH2:16][CH2:15][N:14]3[C:10](=[N:11][C:12]([C:18]4[N:19]([CH:24]([CH3:26])[CH3:25])[N:20]=[C:21]([CH3:23])[N:22]=4)=[CH:13]3)[C:9]=2[CH:27]=1)[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 683128551-[8-Fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-yl]ethanol

Product 1

HCID 683131309-(1-bromoethyl)-8-fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azuleneYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Phosphorus tribromide (0.53 mL of a 1.0 M solution in DCM) was added to a solution of 1-[8-fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-yl]ethanol (98 mg, 0.26 mmol) in DCM (1 mL) at 0° C. The mixture was warmed to RT and stirred for 20 h. Water (2 mL) and sat. NaHCO3 (2 mL) were added and the mixture was extracted with DCM. The combined organics were washed (brine), dried (Na2SO4) and concentrated in vacuo to give the title compound (100 mg, 0.23 mmol, 88%) as a pale yellow solid. The product was taken on without further purification. 1H NMR (CDCl3, 300 MHz): δ 8.72 (1H, d, J=8.7 Hz), 7.60 (1H, s), 6.75 (1H, d, J=11.0 Hz), 5.82 (1H, sept., J=6.6 Hz), 5.45 (1H, q, J=7.0 Hz), 4.52-4.49 (2H, m), 4.44-4.41 (2H, m), 2.42 (3H, s), 2.11 (3H, d, J=7.0 Hz), 1.60 (6H, d, J=6.6 Hz)

Workup

  1. extractionthe mixture was extracted with DCM
  2. washThe combined organics were washed (brine)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2cbb9fc1763d4dcd8e4761afda20e42e
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

Loading…