Perfluoro-1-butanesulfonyl fluoride → HCID 59596643, compound

HRID 2264894Notes

Reaction equation

HRID 2264894 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH3:15])[C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[OH:16])=[O:5])[CH3:2].CCN(C(C)C)C(C)C.[F:26][C:27]([F:42])([C:38]([F:41])([F:40])[F:39])[C:28]([F:37])([F:36])[C:29]([F:35])([F:34])[S:30](F)(=[O:32])=[O:31]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH3:15])[C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[O:16][S:30]([C:29]([F:34])([F:35])[C:28]([F:36])([F:37])[C:27]([F:26])([F:42])[C:38]([F:41])([F:40])[F:39])(=[O:32])=[O:31])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 81531DiisopropylethylamineHCID 59596629HCID 59596629, compound

Product 1

HCID 59596643HCID 59596643, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-hydroxy-1-methyl-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (695 mg, 3.16 mmol) and DMAP (19 mg, 0.16 mmol) in DCM (10 ml) at 0° C. was added DIPEA (1.35 ml, 7.58 mmol) and nonafluorobutylsulfonyl fluoride (0.74 ml, 4.10 mmol). After 10 minutes the reaction was warmed to room temperature and stirred for an additional 4.5 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 then filtered and evaporated to give a yellow oil. The oil was purified by flash chromatography (Si-PPC, pentane:ethyl acetate, gradient 100:0 to 60:40) to afford the title compound as a colourless oil which crystallised on standing (1.43 g, 90%). LCMS (method B): RT=3.28 min, M+H+=505.

Workup

  1. washwashed with water (30 ml)
  2. customThe organic phase was isolated
  3. dry with materialdried over sodium sulphate
  4. filtrationthen filtered
  5. customevaporated
  6. customto give a yellow oil
  7. customThe oil was purified by flash chromatography (Si-PPC, pentane:ethyl acetate, gradient 100:0 to 60:40)

Sources & evidence

ORD record
ord-25cc894c4b794aa2807ef2cdda792d9c
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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