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

HRID 1038135Notes

Reaction equation

HRID 1038135 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=3)[N:10]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:9]=2)=[CH:4][C:3]=1[OH:39].Br[CH2:41][CH2:42][O:43][CH3:44]>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=3)[N:10]([C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:9]=2)=[CH:4][C:3]=1[O:39][CH2:41][CH2:42][O:43][CH3:44]

Participants

5

Reactant 2

HCID 809722-Bromoethyl methyl etherHCID 68966783HCID 68966783, compound

Product 1

HCID 689643693-[4-fluoro-3-(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-(4-fluoro-3-hydroxyphenyl)-5-nitro-1-trityl-1H-indazole 7AU (2 g, 3.88 mmol) in DMF (25 mL) was added CsCO3 1.9 g, 5.82 mmol) and bromoethylmethyl ether (474 μL, 5.04 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-[4-fluoro-3-(2-methoxy-ethoxy)-phenyl]-1-trityl-5-nitro-1H-indazole 8AU (1.8 g) as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-e34b7ec106504a1b81976bc77f65fea8
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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