2-Bromoethyl methyl ether → 3-[3-fluoro-4-(2-methoxy-ethoxy)-phenyl]-1-trityl-5-nitro-1H-indazole

HRID 1038138Notes

Reaction equation

HRID 1038138 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=3)[N:11]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].Br[CH2:41][CH2:42][O:43][CH3:44]>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=3)[N:11]([C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:10]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:41][CH2:42][O:43][CH3:44]

Participants

5

Reactant 2

HCID 809722-Bromoethyl methyl etherHCID 1363872103-(3-fluoro-4-hydroxyphenyl)-5-nitro-1-trityl-1H-indazole

Product 1

HCID 689643703-[3-fluoro-4-(2-methoxy-ethoxy)-phenyl]-1-trityl-5-nitro-1H-indazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of 3-(3-fluoro-4-hydroxyphenyl)-5-nitro-1-trityl-1H-indazole 3AW (3 g, 5.82 mmol) in DMF (40 mL) was added CsCO3 (2.85 g, 8.75 mmol) and bromoethylmethyl ether (711 μL, 7.57 mmol). The resulting mixture was stirred at rt for overnight then diluted with EtOAc (300 mL), which was washed with brine, dried (MgSO4) and concentrated. Chromatograph on silica gel (2:1, hexanes/EtOAc) gave 3-[3-fluoro-4-(2-methoxy-ethoxy)-phenyl]-1-trityl-5-nitro-1H-indazole 4AW (2.8 g).

Workup

  1. washwas washed with brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-379479dd55d24f6a9ed66c25694dc807
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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