Ammonium Chloride → (2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)thiazolo[5,4-b]pyridine-5-yl)(phenyl)methanol

HRID 1177438Notes

Reaction equation

HRID 1177438 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])[N:16]=3)=[C:9]([F:30])[CH:8]=1.[BH4-].[Na+].[NH4+].[Cl-]>CO.C1COCC1>[O:3]1[CH2:4][CH2:5][CH2:6][O:1][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([CH:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[OH:23])[N:16]=3)=[C:9]([F:30])[CH:8]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 67111595(2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)thiazolo[5,4-b]pyridine-5-yl)(phenyl)methanone

Product 1

HCID 67111464(2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)thiazolo[5,4-b]pyridine-5-yl)(phenyl)methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of (2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)thiazolo[5,4-b]pyridine-5-yl)(phenyl)methanone (718.0 mg, 1708 μmol) in methanol (12.0 mL) and THF (4.8 mL) was added sodium borohydride (64.6 mg, 1708 μmol), and the resulting solution was stirred at 25° C. for 10 min. Saturated aqueous NH4Cl (10 mL) was then added, and MeOH and THF were removed in vacuo. The resulting suspension was partitioned between ethyl acetate and water). The organic layer was separated and washed with brine, and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to provide (2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)thiazolo[5,4-b]pyridine-5-yl)(phenyl)methanol as a yellow solid. MS (ESI) m/z: Calculated: 422.1; Observed: 423.0 (M++1).

Workup

  1. customMeOH and THF were removed in vacuo
  2. customThe resulting suspension was partitioned between ethyl acetate and water)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. extractionthe aqueous layer was extracted with EtOAc
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e627e15f4ec458b8a50c1101ff0459e
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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