Sodium Bicarbonate → HCID 12146855, compound

HRID 731591Notes

Reaction equation

HRID 731591 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][N:18]=2)[NH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[S:28](Cl)(=[O:30])=[O:29].CC(C)([O-])C.[K+].C([O-])(O)=O.[Na+]>C1COCC1>[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[S:28]([N:13]1[C:14]2[C:19](=[N:18][CH:17]=[CH:16][CH:15]=2)[C:11]([CH2:10][CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[CH:12]1)(=[O:30])=[O:29]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 27342732,4-Difluorobenzenesulfonyl ChlorideHCID 114483771,1-Dimethylethyl N-[2-(1H-pyrrolo[3,2-b]pyridin-3-yl)ethyl]carbamateHCID 23665647Potassium tert-butoxide

Product 1

HCID 12146855HCID 12146855, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Boc-4-azatryptamine (1.1 eq.) and 2,4-difluorobenzenesulfonyl chloride (1.0 eq.) in THF at room temperature is treated portionwise with solid potassium t-butoxide (1.2 eq), stirred at room temperature for 16 h, poured into saturated NaHCO3 and extracted with EtOAc. The combined extracts are dried over MgSO4 and concentrated in vacuo to give a residue. Purification of this residue by chromatography (silica gel, EtOAc/hexanes as eluent) affords the title carbamate compound.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined extracts are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give a residue
  5. customPurification of this residue by chromatography (silica gel, EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-8bed8934355048c3a9d5d880708696d7
Source dataset
uspto-grants-2009_09
Patent number
US07585876B2

Reaction notes

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