3-Chlorobenzoic Acid → HCID 74220671, compound
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.[Cl:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](O)=[O:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O>C(Cl)Cl>[Cl:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24]([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:25]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 2-(4-iodo-2-methoxy-pyridin-3-yl)-1H-indol-6-ylamine (50 mg, 0.14 mmol) in CH2Cl2 (5 mL) was added 3-chlorobenzoic acid (21 mg, 0.14 mmol) and HATU (52 mg, 0.14 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 3-chloro-N-[2-(4-iodo-2-methoxy-pyridin-3-yl)-1H-indol-6-yl]-benzamide (56 mg, 81%) as a white solid. MH+ 503.8.
Workup
- extractionThe aqueous phase was extracted three times with ethyl acetate
- washThe combined organic layers were washed with brine
- dry with materialdried over magnesium sulfate
- filtrationFiltration
- concentrationfollowed by concentration in vacuo
- customgave a brown solid
Sources & evidence
- ORD record
- ord-6dfe5c4b24b8426e9b94b4945448f29f
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388166B2
Reaction notes
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