Sodium Bicarbonate → HCID 12146855, compound

HRID 1593502Notes

Reaction equation

HRID 1593502 reaction equation
[C:1]([O:5][C:6]([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:7])([CH3:4])([CH3:3])[CH3:2].[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>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][C:11]1[C:19]2=[N:18][CH:17]=[CH:16][CH:15]=[C:14]2[N:13]([S:28]([C:22]2[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=2[F:20])(=[O:30])=[O:29])[CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

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-8f2a8fb20ea248e59af9db935d44ef9b
Source dataset
uspto-grants-2007_11
Patent number
US07297705B2

Reaction notes

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