Hydrochloric Acid → HCID 22603695, compound

HRID 2308101Notes

Reaction equation

HRID 2308101 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([OH:13])=[O:12])[S:10][C:3]=12.[CH3:14][C:15]1[NH:16][CH:17]2[CH:22]([CH:23]=1)[CH:21]=[C:20]([OH:24])[CH:19]=[CH:18]2.C([O-])([O-])=O.[Cs+].[Cs+].C([O-])(O)=O.[Na+].Cl>CCOC(C)=O.CO.CS(C)=O>[CH3:14][C:15]1[NH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][C:20]([O:24][C:2]1[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]([OH:13])=[O:12])[S:10][C:3]=13)=[CH:19][CH:18]=2

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 112760337-Chlorothieno[3,2-b]pyridine-2-carboxylic acidHCID 22603666HCID 22603666, compound

Product 1

HCID 22603695HCID 22603695, compoundYield 76.2%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
165 °C

Procedure

To a solution of 3 mL of DMSO was added 7-Chloro-thieno[3,2-b]pyridine-2-carboxylic acid (0.6 g, 2.63 mmol), 2-Methyl-3a,7a-dihydro-1H-indol-5-ol (0.42 g, 2.63 mmol), MeOH (0.5 mL) and Cs2CO3 (1.7 g, 5.35 mmol) then sealed and warmed to 165° C. for 3 h and cooled to 25° C. To the reaction solution was added 50 mL of EtOAc then portioned between 50/50 NaHCO3 (50 mL). The aqueous layer was then acidified using concentrated HCl drop wise to afford 7-(2-Methyl-1H-indol-5-yloxy)-thieno[3,2-b]pyridine-2-carboxylic acid (0.65 g, 76%) as a white solid. HPLC: Rt 3.62 min. (92% area). 1H NMR (DMSO-d3, 400 MHz) δ: 11.07 (1H, s), 8.45 (1H, d, J=5.3 Hz), 7.98 (1H, s), 7.23 (1H, d, J=8.9 Hz), 7.19 (1H, d, J=7.5, 3.4 Hz), 6.78 (1H, dd, J=6.3, 2.3 Hz) 6.57 (1H, d, J=5.5 Hz), 6.03 (1H, s), 2.26 (3H, s). LCMS (ACPI) M+H+ m/z: 325.

Workup

  1. customthen sealed
  2. temperaturecooled to 25° C

Sources & evidence

ORD record
ord-eac08748c7bb46568219ce681a742547
Source dataset
uspto-grants-2004_12
Patent number
US06833456B2

Reaction notes

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