Water → HCID 74220603, compound

HRID 1051213Notes

Reaction equation

HRID 1051213 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14]([NH2:19])[CH:13]=2.[F:20][CH:21]([F:25])[C:22](O)=[O:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O>C(Cl)Cl>[F:20][CH:21]([F:25])[C:22]([NH:19][C:14]1[CH:13]=[C:12]2[C:17]([CH:18]=[C:10]([C:3]3[C:4]([O:8][CH3:9])=[N:5][CH:6]=[CH:7][C:2]=3[I:1])[NH:11]2)=[CH:16][CH:15]=1)=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 9788Difluoroacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90103105HCID 90103105, compound

Product 1

HCID 74220603HCID 74220603, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(4-iodo-2-methoxy-pyridin-3-yl)-1H-indol-6-ylamine (30 mg, 0.08 mmol) in CH2Cl2 (5 mL) was added 2,2-difluoroacetic acid (12 mg, 0.12 mmol) and HATU (47 mg, 0.12 mol). The solution was stirred at 25° C. for 1 h and poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave a brown solid. Flash chromatography (70/30 hexanes/ethyl acetate) afforded 2,2-difluoro-N-[2-(4-iodo-2-methoxy-pyridin-3-yl)-1H-indol-6-yl]-acetamide (24 mg, 67%) as a white solid. MH+ 443.9.

Workup

  1. extractionThe aqueous phase was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration
  5. concentrationfollowed by concentration in vacuo
  6. customgave a brown solid

Sources & evidence

ORD record
ord-24fe26d9799f4da79aea5d7d25d6204b
Source dataset
uspto-grants-2016_07
Patent number
US09388166B2

Reaction notes

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