Dimethylformamide → HCID 23393847, compound

HRID 966513Notes

Reaction equation

HRID 966513 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[CH:8][C:7]([OH:21])=[CH:6][CH:5]=2.CN(C=O)C.C(N(CC)CC)C.[F:34][C:35]([F:50])([S:46](F)(=[O:48])=[O:47])[C:36]([F:45])([F:44])[C:37]([F:43])([F:42])[C:38]([F:41])([F:40])[F:39]>C(Cl)Cl.C(Cl)Cl.CO>[CH2:14]([O:13][C:11]([C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:21][S:46]([C:35]([F:34])([F:50])[C:36]([F:44])([F:45])[C:37]([F:42])([F:43])[C:38]([F:41])([F:40])[F:39])(=[O:48])=[O:47])[CH:8]=2)[NH:3][C:2]=1[CH3:1])=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 109239755-Hydroxy-2-methyl-1H-indole-3-carboxylic acid benzyl ester

Product 1

HCID 23393847HCID 23393847, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

2-Methyl-3-benzyloxycarbonyl-5-hydroxyindole (5.90 g, 21.0 mmol, 1 eq) was suspended in dry CH2Cl2 (100 mL) and dry DMF (2 mL) under Ar. Triethylamine (8.77 mL, 63 mmol, 3 eq) was added followed by the addition of perfluorobutanesulfonyl fluoride (4.2 mL, 23.4 mmol, 1.1 eq). The reaction mixture was stirred at room temperature and followed by TLC (CH2Cl2/MeOH 98/2). After 18 hours, the reaction was quenched with aqueous hydrochloric acid. The organic phase was washed with water (2×) and the combined aqueous phases extracted with CH2Cl2. The combined organic extracts were washed with brine and dried over Na2SO4. After removing the solvent, the residue was loaded on silica gel and chromatographed eluting with methanol/CH2Cl2(98/2). 10.17 g (86% yield) of the indole-nonaflate was obtained as a white solid.

Workup

  1. customthe reaction was quenched with aqueous hydrochloric acid
  2. washThe organic phase was washed with water (2×)
  3. extractionthe combined aqueous phases extracted with CH2Cl2
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. customAfter removing the solvent
  7. customchromatographed
  8. washeluting with methanol/CH2Cl2(98/2)

Sources & evidence

ORD record
ord-75b073e6b59b485b9db7d1387b2b4eab
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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