Triethylamine → 2-{5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethyl methanesulphonate

HRID 1916711Notes

Reaction equation

C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21]#[C:22][C:23]3[CH:24]=[C:25]4[C:29](=[CH:30][CH:31]=3)[N:28]([CH2:32][CH2:33][OH:34])[CH:27]=[CH:26]4)=[N:19][CH:20]=2)=[CH:11][CH:10]=1.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C1COCC1.N1C=CC=CC=1>[CH3:35][S:36]([O:34][CH2:33][CH2:32][N:28]1[C:29]2[C:25](=[CH:24][C:23]([C:22]#[C:21][C:18]3[CH:17]=[CH:16][C:15]([C:12]4[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][CH:13]=4)=[CH:20][N:19]=3)=[CH:31][CH:30]=2)[CH:26]=[CH:27]1)(=[O:38])=[O:37]

Participants

Conditions

Temperature: 0 °C

Procedure

Under an argon atmosphere 7.1 mL (51.5 mmol) triethylamine are added to a solution of 16.0 g (42.9 mmol) 2-{5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethanol in 480 mL THF and 30 mL pyridine and this is cooled to 0° C. Then a solution of 4 mL (51.5 mmol) methanesulphonic acid chloride in 20 mL THF is slowly added dropwise, the mixture is allowed to warm up to RT and stirred for a further 2 h at RT. The reaction solution is filtered and evaporated down i.vac. The residue is combined with 1 L DCM, washed with 400 mL water and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is suspended with 600 mL PE/DCM (5:1), suction filtered and finally dried in the air until a constant weight is obtained.

Workup

temperatureto warm up to RT
filtrationThe reaction solution is filtered
customevaporated down i.vac
washwashed with 400 mL water
dry with materialthe organic phase is dried over Na2SO4
filtrationfiltered
customfinally dried in the air until a constant weight
customis obtained

Sources & evidence

ORD record: ord-93d5cc7dd2aa419abcc735b0d1982659
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618132B2

Reaction notes

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