Ammonium Chloride → (2-{7-(Benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-1,3-thiazol-5-yl)methanol

HRID 1188988Notes

Reaction equation

HRID 1188988 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:28][C:29]2[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]1[S:19][C:20]([C:23](OCC)=[O:24])=[CH:21][N:22]=1)=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H][H].[Cl-].[NH4+]>O1CCCC1.C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:28][C:29]2[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:36])=[O:37])=[CH:31][CH:30]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]1[S:19][C:20]([CH2:23][OH:24])=[CH:21][N:22]=1)=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 66897604Ethyl 2-{7-(benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-1,3-thiazole-5-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 67118479(2-{7-(Benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-1,3-thiazol-5-yl)methanolYield 23.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 2-{7-(benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-1,3-thiazole-5-carboxylate (242 mg) in tetrahydrofuran (25 mL) was added lithium aluminum hydride (50 mg) at 0° C. After the mixture was stirred at 0° C. for 30 min, ethanol was added dropwise until hydrogen did not generate. A saturated aqueous ammonium chloride solution was added to the mixture and the resulting yellow suspension was filtered through celite. The filtrate was concentrated and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80 to 100/0, volume ratio) to give yellow crystals. The crystals were recrystallized from ethanol-ethyl acetate to give yellow crystals. The crystals were purified by silica gel column chromatography (ethyl acetate/hexane=20/80 to 90/10, volume ratio) to give yellow crystals. The crystals were recrystallized from ethanol-hexane to give the title compound (52 mg, 23%) as yellow crystals. MS 507 (MH+). mp 125-126° C.

Workup

  1. filtrationthe resulting yellow suspension was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80 to 100/0, volume ratio)
  4. customto give yellow crystals
  5. customThe crystals were recrystallized from ethanol-ethyl acetate
  6. customto give yellow crystals
  7. customThe crystals were purified by silica gel column chromatography (ethyl acetate/hexane=20/80 to 90/10, volume ratio)
  8. customto give yellow crystals
  9. customThe crystals were recrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-03a0b6719f0647fbb82081020bc5380a
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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