Triethylamine → Tert-butyl 6-bromo-3,3-bis((methylsulfonyloxy)methyl)-2-oxoindoline-1-carboxylate

HRID 1618782Notes

Reaction equation

HRID 1618782 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:21][OH:22])([CH2:19][OH:20])[C:7](=[O:18])[N:8]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:19][O:20][S:31]([CH3:30])(=[O:33])=[O:32])([CH2:21][O:22][S:31]([CH3:30])(=[O:33])=[O:32])[C:7](=[O:18])[N:8]2[C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58221668Tert-butyl 6-bromo-3,3-bis(hydroxymethyl)-2-oxoindoline-1-carboxylate

Product 1

HCID 58221521Tert-butyl 6-bromo-3,3-bis((methylsulfonyloxy)methyl)-2-oxoindoline-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of tert-butyl 6-bromo-3,3-bis(hydroxymethyl)-2-oxoindoline-1-carboxylate (5.27 g, 14.16 mmol) in DCM (94 mL) was added triethylamine (7.89 mL, 56.6 mmol) followed by methanesulfonyl chloride (2.21 mL, 28.3 mmol). The solution was stirred for 1 h and then it was concentrated under reduced pressure. Purification by column chromatography (eluting with a gradient of 10-60% EtOAc in hexanes) gave tert-butyl 6-bromo-3,3-bis((methylsulfonyloxy)methyl)-2-oxoindoline-1-carboxylate as a white foam. Mass Spectrum (ESI) m/e=550.0 [(M+Na+) (79Br)] and 552.0 [(M+Na+) (81Br)].

Workup

  1. concentrationit was concentrated under reduced pressure
  2. customPurification by column chromatography (
  3. washeluting with a gradient of 10-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bfd72aabcf9b4facb818a1e4e5d4f77d
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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