2-Methyl-2-butene → 3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzoic acid

HRID 1177395Notes

Reaction equation

HRID 1177395 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20]1)[N:13]=2)[CH:5]=[O:6].O.P([O-])(O)(O)=[O:30].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>O.CC(O)(C)C>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:20][CH2:21]1)[N:13]=2)[C:5]([OH:30])=[O:6]

Participants

6

Reactant 4

HCID 105532-Methyl-2-buteneHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 591749073-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde

Product 1

HCID 573944063-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

To a slurry of 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)-benzaldehyde (3.80 g, 10.1 mmol) and sodium dihydrogenphosphate hydrate (7.00 g, 50.7 mmol) in 40 mL 1:1 water/t-BuOH under nitrogen was added 2-methylbut-2-ene (37.6 mL, 355 mmol) and sodium chlorite (4.59 g, 50.7 mmol). The reaction mixture was allowed to stir rapidly for 3 days. The thick reaction mixture was concentrated in vacuo to remove the 2-methyl-2-butene, and the slurry diluted with water and filtered, rinsing water and MeOH. The resulting solid was dried in vacuo to give 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzoic acid as an off-white solid which was used without further purification. MS (ESI) m/z: Calculated: 390.1; Observed: 391.1 (M++1).

Workup

  1. concentrationThe thick reaction mixture was concentrated in vacuo
  2. customto remove the 2-methyl-2-butene
  3. additionthe slurry diluted with water
  4. filtrationfiltered
  5. washrinsing water and MeOH
  6. customThe resulting solid was dried in vacuo

Sources & evidence

ORD record
ord-0794de6c89164fa89735f0f03c8d17e9
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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