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Perfluoro-1-butanesulfonyl fluoride → 3-(Nonafluorobutane-1-sulfonyloxy)-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester

HRID 1366772
Notes
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Reaction equation

HRID 1366772 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:14][C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[OH:15])=[O:5])[CH3:2].CCN(C(C)C)C(C)C.[F:25][C:26]([F:41])([C:37]([F:40])([F:39])[F:38])[C:27]([F:36])([F:35])[C:28]([F:34])([F:33])[S:29](F)(=[O:31])=[O:30]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[S:14][C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[O:15][S:29]([C:28]([F:33])([F:34])[C:27]([F:35])([F:36])[C:26]([F:25])([F:41])[C:37]([F:40])([F:39])[F:38])(=[O:31])=[O:30])=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 81531DiisopropylethylamineHCID 597039163-Hydroxy-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 597039083-(Nonafluorobutane-1-sulfonyloxy)-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-hydroxy-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester (1.3 g, 5.82 mmol) and DMAP (35 mg, 0.29 mmol) in DCM (10 ml) at 0° C. was added DIPEA (2.5 ml, 14.0 mmol) and nonafluorobutylsulfonyl fluoride (1.36 ml, 7.56 mmol). After 10 minutes the reaction mixture was warmed to room temperature and stirred for an additional 20 hours. The reaction mixture was diluted with DCM (50 ml) and washed with water (30 ml). The organic phase was isolated, dried over sodium sulphate, filtered and evaporated to give a brown oil. The oil was purified by flash chromatography (Si-SPE, pentane:diethyl ether, gradient 100:0 to 70:30) to afford the title compound as a colourless oil which crystallised on standing (420 mg, 14%). LCMS (method B): RT=4.46 min, M+H+=508.

Workup

  1. washwashed with water (30 ml)
  2. customThe organic phase was isolated
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a brown oil
  7. customThe oil was purified by flash chromatography (Si-SPE, pentane:diethyl ether, gradient 100:0 to 70:30)

Sources & evidence

ORD record
ord-e98db72ae9e64c35b94c615af2a9ae20
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07893085B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes