Potassium Carbonate → 1-(2-chloro-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole

HRID 237423Notes

Reaction equation

[CH3:1][S:2]([CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2)(=[O:4])=[O:3].[Cl:18][C:19]1[N:24]=[C:23](Cl)[CH:22]=[CH:21][N:20]=1.C1C=CC2N(O)N=NC=2C=1.C([O-])([O-])=O.[K+].[K+]>CC(O)C.CC(N(C)C)=O>[Cl:18][C:19]1[N:24]=[C:23]([N:13]2[C:14]3[C:10](=[C:9]([O:8][CH2:7][CH2:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:17]=[CH:16][CH:15]=3)[CH:11]=[CH:12]2)[CH:22]=[CH:21][N:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-(3-Methanesulfonyl-propoxy)-1H-indole (188.1 g), 2,4-dichloropyrimidine (221.25 g), HOBT (20.08 g), K2CO3 (143.68 g) and DMA (1.6 L) were heated to 85° C. for 20 h. IPA (5 was then added and the mixture was stirred for 20 min, then cooled to 0° C. for 3 h and filtered. The collected solid was rinsed with IPA and water, and the solid was dried in vacuo at 55° C. for 4 days to yield 1-(2-chloro-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole (94%).

Workup

filtrationfiltered
washThe collected solid was rinsed with IPA and water
customthe solid was dried in vacuo at 55° C. for 4 days

Sources & evidence

ORD record: ord-b2cec9eacf5049e1b3e43e2be50e8405
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642601B2

Reaction notes

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