Triethylamine → HCID 89373238, compound

HRID 1912632Notes

Reaction equation

HRID 1912632 reaction equation
[OH:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH3:15])[C:6]=2[N:5]=[C:4]([CH3:16])[C:3]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18].CCN(CC)CC.[O:29](S(C(F)(F)F)(=O)=O)[S:30]([C:33]([F:36])([F:35])[F:34])(=O)=[O:31]>ClCCl>[CH3:16][C:4]1[C:3]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:2]([O:1][S:30]([C:33]([F:36])([F:35])[F:34])(=[O:31])=[O:29])[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH3:15])[C:6]=2[N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 178469168HCID 178469168, compound

Product 1

HCID 89373238HCID 89373238, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

An ice cold mixture of ethyl 4-hydroxy-2,9-dimethyl-9H-pyrido[2,3-b]indole-3-carboxylate (210 mg, 0.739 mmol) in dichloromethane (DCM) (3.5 mL) was treated with Et3N (0.154 mL, 1.108 mmol) and Tf2O (0.137 mL, 0.812 mmol), and then stirred at 0° C. for 90 min. The mixture was concentrated and purified with column chromatography (0-100% DCM/Hexane) to afford ethyl 2,9-dimethyl-4-(((trifluoromethyl)sulfonyl)oxy)-9H-pyrido[2,3-b]indole-3-carboxylate (286.8 mg, 0.689 mmol, 93% yield) as white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.23 (d, J=7.9 Hz, 1 H), 7.65-7.57 (m, 1 H), 7.49 (d, J=8.2 Hz, 1 H), 7.42-7.34 (m, 1 H), 4.46 (q, J=7.1 Hz, 2 H), 3.98 (s, 3 H), 2.88 (s, 3 H), 1.45 (t, 3 H); LCMS (m/z) ES+=417 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified with column chromatography (0-100% DCM/Hexane)

Sources & evidence

ORD record
ord-152a2b4b3b664f3a85885f0b574b01ec
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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