Triethylamine → HCID 86675746, compound

HRID 1912636Notes

Reaction equation

HRID 1912636 reaction equation
[CH:1]1([N:4]2[C:12]3[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=3[C:6]3[C:13]([OH:23])=[C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:15]([CH3:17])=[N:16][C:5]2=3)[CH2:3][CH2:2]1.CCN(CC)CC.[O:31](S(C(F)(F)F)(=O)=O)[S:32]([C:35]([F:38])([F:37])[F:36])(=O)=[O:33]>ClCCl>[CH:1]1([N:4]2[C:12]3[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=3[C:6]3[C:13]([O:23][S:32]([C:35]([F:38])([F:37])[F:36])(=[O:33])=[O:31])=[C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:15]([CH3:17])=[N:16][C:5]2=3)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 178469169HCID 178469169, compound

Product 1

HCID 86675746HCID 86675746, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

An ice cold mixture of ethyl 9-cyclopropyl-4-hydroxy-2-methyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]indole-3-carboxylate (1.362 g, 4.33 mmol) in dichloromethane (DCM) (20 ml) was treated with Et3N (0.906 ml, 6.50 mmol) and Tf2O (0.805 ml, 4.77 mmol), and then stirred at 0° C. for 90 min. The mixture was concentrated and purified with column chromatography (0-50% EtOAc/Hexane, 120 g silica gel) to give ethyl 9-cyclopropyl-2-methyl-4-(((trifluoromethyl)sulfonyl)oxy)-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]indole-3-carboxylate (1.8341 g, 4.11 mmol, 95% yield) as white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.39 (q, J=7.2 Hz, 2 H), 3.17-2.98 (m, 1 H), 2.90-2.78 (m, 4 H), 2.75 (s, 3 H), 1.99-1.88 (m, 2 H), 1.88-1.76 (m, 2 H), 1.40 (t, J=7.2 Hz, 3 H), 1.22-1.07 (m, 4 H); LCMS (m/z) ES+=447 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified with column chromatography (0-50% EtOAc/Hexane, 120 g silica gel)

Sources & evidence

ORD record
ord-9a16c913d0504c028b01d3014f6adc29
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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