Water → Methyl 1-(5-(2-fluorophenyl)pyrimidin-2-yl)-3-methyl-1H-indole-6-carboxylate

HRID 630479Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:15]=2)[NH:10][CH:9]=1.Cl[C:22]1[N:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])=[CH:24][N:23]=1.O>CN(C1C=CN=CC=1)C.CS(C)=O>[F:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:25]1[CH:26]=[N:27][C:22]([N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[C:13]([C:17]([O:19][CH3:20])=[O:18])[CH:12]=3)[C:8]([CH3:7])=[CH:9]2)=[N:23][CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Potassium carbonate (1.61 g, 11.6 mmol) and DMAP (0.18 g, 1.45 mmol) were added to a solution of methyl 3-methyl-1H-indole-6-carboxylate (1.1 g, 5.81 mmol) and 2-chloro-5-(2-fluorophenyl)-pyrimidine (1.21 g, 5.81 mmol) in dry DMSO (10 mL). The solution was stirred at 100° C. for 1 h, then cooled to room temperature and slowly poured into vigorously stirred water (100 mL). The precipitating solid was filtered off, washed with water and dried in vacuum. Light-brown solid. Yield: 1.89 g (80% chemical purity). HPLC-MS: m/z [M+H]+=362.

Workup

temperaturecooled to room temperature
filtrationThe precipitating solid was filtered off
washwashed with water
customdried in vacuum

Sources & evidence

ORD record: ord-468f9f27d5c44e8a9c7395e65b0e6f86
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315490B2

Reaction notes

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