Dimethylformamide → HCID 59625911, compound

HRID 1911210Notes

Reaction equation

HRID 1911210 reaction equation
[F:1][C:2]1[C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16].[C:24](Cl)(=O)C(Cl)=O.CN(C=O)C.CCN(CC)CC>C(Cl)Cl.CO>[F:1][C:2]1[C:10]([C:11]([O:13][CH3:24])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[Si:14]([CH:18]([CH3:20])[CH3:19])([CH:21]([CH3:23])[CH3:22])[CH:15]([CH3:16])[CH3:17]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 11688604HCID 11688604, compound

Product 1

HCID 59625911HCID 59625911, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoro-1-triisopropylsilanyl-1H-indole-5-carboxylic acid 70a (prepared using a procedure described in Eur. J. Org. Chem. 2006, 2956) (8.08 mmol, 2.71 g) in dry CH2Cl2 (20 mL) was added oxalyl chloride (9.69 mmol, 0.82 mL) followed by DMF (0.81 mmol, 0.063 mL). The reaction was stirred at rt for 30 min and then concentrated. The residue was dissolved in CH2Cl2 (20 mL) and cooled to 0° C. Et3N (40.4 mmol, 5.6 mL) was added, followed by slow addition of MeOH. The reaction mixture was stirred at 0° C. for 30 min and concentrated. The residue was partitioned between EtOAc and water. The organic layer was concentrated and purified by flash column chromatography (silica gel, 5% EtOAc/hexanes) to give compound 70b.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in CH2Cl2 (20 mL)
  3. temperaturecooled to 0° C
  4. stirringThe reaction mixture was stirred at 0° C. for 30 min
  5. concentrationconcentrated
  6. customThe residue was partitioned between EtOAc and water
  7. concentrationThe organic layer was concentrated
  8. custompurified by flash column chromatography (silica gel, 5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-54df8b11b6644aa3ba2e624f245d9424
Source dataset
uspto-grants-2013_12
Patent number
US08604017B2

Reaction notes

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