Tetrahydrofuran → HCID 67112718, compound

HRID 1177502Notes

Reaction equation

HRID 1177502 reaction equation
CC1C=CC(S(NN)(=O)=O)=CC=1.[F:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[C:21]1[S:22][C:23]2[C:28]([N:29]=1)=[CH:27][CH:26]=[C:25]([C:30]1([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:33][C:32](=O)[CH2:31]1)[N:24]=2.C([BH3-])#N.[Na+].C1COCC1>CO.[Cl-].[Zn+2].[Cl-]>[F:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[C:21]1[S:22][C:23]2[C:28]([N:29]=1)=[CH:27][CH:26]=[C:25]([C:30]1([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH2:31][CH2:32][CH2:33]1)[N:24]=2

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 15303P-ToluenesulfonylhydrazideHCID 5003444Sodium cyanoborohydrideHCID 67111551HCID 67111551, compound

Product 1

HCID 67112718HCID 67112718, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Conditions

Temperature
70 °C

Procedure

To a thick slurry of p-methylbenzenesulfonylhydrazine (0.036 g, 0.19 mmol) and 3-(2-(2-fluoro-4-methylphenyl)thiazolo[5,4-b]pyridine-5-yl)-3-phenylcyclobutanone (0.050 g, 0.13 mmol) in 0.3 mL MeOH under nitrogen was added a pre-mixed suspension of sodium cyanoborohydride (0.016 g, 0.26 mmol) and zinc chloride, 0.5 M solution in THF (0.26 mL, 0.13 mmol) in 0.26 mL MeOH, via pipette. The reaction mixture was sealed and heated to 70° C. for 3 h. The reaction mixture was adsorbed onto 600 mg silica gel and dried. Purification by silica gel chromatography, 12 g, 0-50% EA/hexanes provided 2-(2-fluoro-4-methylphenyl)-5-(1-phenylcyclobutyl)-thiazolo[5,4-b]pyridine as a light yellow oil that slowly solidified. MS (ESI) m/z: calculated: 374.1; Observed: 375.1 (M++1).

Workup

  1. customThe reaction mixture was sealed
  2. customdried
  3. customPurification by silica gel chromatography, 12 g, 0-50% EA/hexanes

Sources & evidence

ORD record
ord-9ff376ea051d446f9d9bdbcd3284754f
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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