Triethylamine → HCID 59332646, compound

HRID 387294Notes

Reaction equation

HRID 387294 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11](O)=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:14][CH:15]1[CH2:20][CH2:19][S:18](=[O:22])(=[O:21])[CH2:17][CH2:16]1.CC[N:25](CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.N.CO>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:25])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:14][CH:15]1[CH2:20][CH2:19][S:18](=[O:22])(=[O:21])[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21705897Ammonia methanolHCID 59332629HCID 59332629, compound

Product 1

HCID 59332646HCID 59332646, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-3-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methyl]-1H-indole-7-carboxylic acid (1.2 g, 3.22 mmol) in CH2Cl2 (100 mL) was added Et3N (650 mg, 6.44 mmol), TBTU (2.1 g, 6.44 mmol), and NH3/MeOH (10 mL). The mixture was stirred for 2 hours at room temperature. The reaction solution was washed with water, and the organic phase was dried (MgSO4), concentrated, and purified by column chromatography on silica gel, giving 770 mg (65%) of the title compound.

Workup

  1. washThe reaction solution was washed with water
  2. dry with materialthe organic phase was dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-747eea31936c4b5d9fd9021795999dc8
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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