Water → HCID 136348393, compound

HRID 718837Notes

Reaction equation

HRID 718837 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([OH:25])[CH:23]=3)[CH:18]=[N:17]2)=[CH:12][CH:11]=1.C1COCC1.O>CCOC(C)=O>[Br:8][C:23]1[C:22]([OH:25])=[CH:21][CH:20]=[C:19]2[C:24]=1[N:16]([C:13]1[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=1)[N:17]=[CH:18]2

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 67184N-bromobutanimideHCID 136348392HCID 136348392, compound

Product 1

HCID 136348393HCID 136348393, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

NBS (16.2 g, 91 mmol) was added in one portion to a solution of 1-(4-fluorophenyl)-1H-indazol-6-ol (96, R1=4-Fluorophenyl) (20.3 g, 89 mmol) and THF (500 mL) under a nitrogen atmosphere at about 0° C. After about 1 h, water (500 mL) and EtOAc (400 mL) were added. The layers were separated and the aqueous layer was extracted with EtOAc (100 mL). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting solid was slurried in DCM (50 mL) then collected by filtration rinsing with DCM (4×25 mL). The solid was dried to afford 7-bromo-1-(4-fluorophenyl)-1H-indazol-6-ol (97, R1=4-Fluorophenyl) (17.2 g, 63% yield) as a faint orange solid. LC/MS, method 3, Rt=2.02 min, MS m/z 307 and 309 (M+H)+. 1H NMR (400 MHz, DMSO) δ 10.52 (d, J=0.9 Hz, 1H), 8.20 (d, J=0.9 Hz, 1H), 7.67 (dd, J=8.6, 0.9 Hz, 1H), 7.54-7.47 (m, 2H), 7.38-7.29 (m, 2H), 6.95 (dd, J=8.6, 0.9 Hz, 1H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc (100 mL)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. filtrationthen collected by filtration
  7. washrinsing with DCM (4×25 mL)
  8. customThe solid was dried

Sources & evidence

ORD record
ord-d1e9afd1f8334497bfb83b931d4b6416
Source dataset
uspto-grants-2015_11
Patent number
US09193744B2

Reaction notes

Loading…