HCID 90418039, compound → HCID 90418726, compound

HRID 2177300Notes

Reaction equation

HRID 2177300 reaction equation
[CH2:1]([C:3]1[C:7]([C:8](O)=[O:9])=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=2[F:18])[S:5][N:4]=1)[CH3:2]>O1CCCC1>[CH2:1]([C:3]1[C:7]([CH2:8][OH:9])=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=2[F:18])[S:5][N:4]=1)[CH3:2]

Participants

3

Reactant 1

HCID 90418039HCID 90418039, compound

Product 1

HCID 90418726HCID 90418726, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 3-ethyl-5-(2-fluoro-4-methylphenyl)-1,2-thiazole-4-carboxylic acid (150 mg, 0.57 mmol, 1.00 equiv), tetrahydrofuran (10 mL). This was followed by the addition of BH3 (1.7 mL) at 0-5° C. The resulting solution was stirred overnight at 20° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:2). This resulted in 50 mg (35%) of [3-ethyl-5-(2-fluoro-4-methylphenyl)-1,2-thiazol-4-yl]methanol as colorless oil.

Workup

  1. customInto a 25-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. additionThis was followed by the addition of BH3 (1.7 mL) at 0-5° C
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. customThis resulted in 50 mg (35%) of [3-ethyl-5-(2-fluoro-4-methylphenyl)-1,2-thiazol-4-yl]methanol as colorless oil

Sources & evidence

ORD record
ord-c33203fa1d204cf7aa170a0f41a88a42
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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