Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Difluoroacetic acid | HCID 9788 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | HCID 74220604 | HCID 74220604 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 74220668 | HCID 74220668 | 33% |
Reaction Steps
A solution of [2-(4-iodo-2-methoxy-pyridin-3-yl)-1H-indol-6-yl]-methyl-amine (30 mg, 0.08 mmol) in CH2Cl2 (5 mL) was added 2,2-difluoroacetic acid (11 mg, 0.12 mmol) and HATU (45 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]-N-methyl-acetamide (12 mg, 33%) as a white solid. MH+ 457.8.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09388166B2 |
|---|
| Source dataset | uspto-grants-2016_07 |
|---|
| ORD ID | ord-025087805d2d4874914a309c3d1e5c26 |
|---|
| Source note | uspto-grants-2016_07 |
|---|
