Dimethylformamide → Ammonium Hydroxide

HRID 889894Notes

Reaction equation

HRID 889894 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][CH:13]=[C:14]([C:16]([OH:19])([CH3:18])[CH3:17])[N:15]=3)[S:10][C:3]=12.CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:31][C:32]1[NH:33][C:34]2[C:39]([CH:40]=1)=[CH:38][C:37]([OH:41])=[CH:36][CH:35]=2>CO.C(Cl)(Cl)Cl>[NH4+:5].[OH-:19].[CH3:31][C:32]1[NH:33][C:34]2[C:39]([CH:40]=1)=[CH:38][C:37]([O:41][C:2]1[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]4[S:12][CH:13]=[C:14]([C:16]([OH:19])([CH3:18])[CH3:17])[N:15]=4)[S:10][C:3]=13)=[CH:36][CH:35]=2

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 833362-methyl-1H-indol-5-olHCID 221436652-[2-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-thiazol-4-yl]-propan-2-ol

Product 2

HCID 14923Ammonium HydroxideHCID 10202393HCID 10202393, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 2-[2-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-thiazol-4-yl]-propan-2-ol (100 mg, 0.322 mmol), DMF 0.7 mL, cesium carbonate (210 mg, 0.644 mmol) and 2-methyl-1H-indol-5-ol and (95.0 mg, 0.644 mmol) was heated to 85° C. for sixteen hours. The reaction mixture was cooled to room temperature and extracted with 5% methanol/ethyl acetate and water. The layers were separated, and the aqueous layer was washed with a 5% methanol and ethyl acetate solution. The combined organic layers were washed with brine, dried over magnesium sulfate, and evaporated under reduced pressure to give an oily brown solid. Silica gel chromatography (98:1.8:0.2 CHCl3:CH3OH:NH4OH) afforded the titled compound (46 mg) as an off-white solid in 17% yield. C22H19N3O2S2: APCI m/z 422.2 (pos.); 1H NMR (CD3OD): δ 8.38 (d, 1H, J=5.6 Hz), 7.89 (s, 1H), 7.47 (s, 1H), 7.35 (d, 1H, J=8.7 Hz), 7.26 (s, 1H), 6.87 (d, 1H, J=8.7 Hz), 6.57 (d, 1H, J=5.6 Hz), 6.17 (s, 1H), 2.43 (s, 3H), 1.61 (s, 6H) ppm.

Workup

  1. extractionextracted with 5% methanol/ethyl acetate and water
  2. customThe layers were separated
  3. washthe aqueous layer was washed with a 5% methanol and ethyl acetate solution
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto give an oily brown solid

Sources & evidence

ORD record
ord-6e231608b2134782991967f1df11830d
Source dataset
uspto-grants-2006_02
Patent number
US06995171B2

Reaction notes

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