Methanol → HCID 178496975, compound

HRID 1978955Notes

Reaction equation

HRID 1978955 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:20])=[C:12]3[CH:18]=[C:17](I)[S:16][C:13]3=[N:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:30][OH:31].C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN([CH:64]=[O:65])C>CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:20])=[C:12]3[CH:18]=[C:17]([C:30]([O:65][CH3:64])=[O:31])[S:16][C:13]3=[N:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 178522942HCID 178522942, compound

Product 1

HCID 178496975HCID 178496975, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
70 °C

Procedure

To a solution of N-(4-chlorobenzyl)-4-hydroxy-2-iodothieno[2,3-b]pyridine-5-carboxamide (2.61 g) from Example No. 2 in DMF (33 mL) are added triethylamine (1.6 mL), methanol (9.5 mL), Pd(OAc)2 (0.132 g), and dppp (0.242 g). Carbon monoxide is bubbled through the solution, and the reaction is heated to 70° C. The reaction is stirred at 70° C. for 18 h. The reaction mixture is cooled to rt, and water (25 mL) and 2 N HCl (25 mL) are added. The resulting precipitate is filtered off and purified by column chromatography (CH2Cl2; CH2Cl2/methanol, 99/1; 98/2). A mixture of starting material and desired product is isolated as a yellow solid. This material is re-subjected to the reaction conditions above. The reaction is stirred at 70° C. for 18 h. The reaction is cooled to rt and water (25 mL) and 2 N HCl (25 mL) are added. The resulting orange solid is filtered off and purified by column chromatography (CH2Cl2;

Workup

  1. customCarbon monoxide is bubbled through the solution
  2. temperatureThe reaction mixture is cooled to rt
  3. additionwater (25 mL) and 2 N HCl (25 mL) are added
  4. filtrationThe resulting precipitate is filtered off
  5. custompurified by column chromatography (CH2Cl2; CH2Cl2/methanol, 99/1; 98/2)
  6. additionA mixture of starting material

Sources & evidence

ORD record
ord-7f2ccaadcc2647e8a2f7c5854b9ccfea
Source dataset
uspto-grants-2001_05
Patent number
US06239142B1

Reaction notes

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