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Sodium hydride → methyl 7-[(2-bromo-4-fluorobenzenesulfonyl)-(2-trimethylsilanyl-ethoxymethyl)-amino]-4H-furo[2,3-c]chromene-6-carboxylate

HRID 1778372
Notes
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Reaction equation

HRID 1778372 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[S:11]([NH:14][C:15]1[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]2[C:18]([C:19]3[CH:31]=[CH:30][O:29][C:20]=3[CH2:21][O:22]2)=[CH:17][CH:16]=1)(=[O:13])=[O:12].[CH3:32][Si:33]([CH3:40])([CH3:39])[CH2:34][CH2:35][O:36][CH2:37]Cl>C1COCC1>[Br:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[S:11]([N:14]([CH2:37][O:36][CH2:35][CH2:34][Si:33]([CH3:40])([CH3:39])[CH3:32])[C:15]1[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]2[C:18]([C:19]3[CH:31]=[CH:30][O:29][C:20]=3[CH2:21][O:22]2)=[CH:17][CH:16]=1)(=[O:12])=[O:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 66685486methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-4H-furo[2,3-c]chromene-6-carboxylate2×

Product 1

HCID 66685296methyl 7-[(2-bromo-4-fluorobenzenesulfonyl)-(2-trimethylsilanyl-ethoxymethyl)-amino]-4H-furo[2,3-c]chromene-6-carboxylateYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in oil, 0.304 g) was added to a stirred solution of methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-4H-furo[2,3-c]chromene-6-carboxylate (Intermediate 7, 2.93 g) in THF (30 mL). The resultant mixture was stirred at room temperature for 5 minutes until effervescence had ceased. 2-(trimethylsilyl)ethoxymethyl chloride (1.27 g) was added and the solution was stirred at room temperature for one hour. The mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate, washed with water, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 0-20% to give methyl 7-[(2-bromo-4-fluorobenzenesulfonyl)-(2-trimethylsilanyl-ethoxymethyl)-amino]-4H-furo[2,3-c]chromene-6-carboxylate (3.51 g) as a white foam.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 0-20%

Sources & evidence

ORD record
ord-a387c4dd7ccf454fa832c95194733501
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09266896B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes