Diisobutylaluminum hydride → 4-(5-(1-Phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde

HRID 1177559Notes

Reaction equation

HRID 1177559 reaction equation
CC(C[AlH]CC(C)C)C.[C:10]1([C:16]2([C:19]3[N:24]=[C:23]4[S:25][C:26]([C:28]5[CH:35]=[CH:34][C:31]([C:32]#N)=[CH:30][CH:29]=5)=[N:27][C:22]4=[CH:21][CH:20]=3)[CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(C(C(C([O-])=O)O)O)([O-])=[O:37]>C(Cl)Cl>[C:10]1([C:16]2([C:19]3[N:24]=[C:23]4[S:25][C:26]([C:28]5[CH:35]=[CH:34][C:31]([CH:32]=[O:37])=[CH:30][CH:29]=5)=[N:27][C:22]4=[CH:21][CH:20]=3)[CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 38061142,3-DihydroxybutanedioateHCID 671129224-(5-(1-Phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzonitrile

Product 1

HCID 866387254-(5-(1-Phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

DIBAL-H (1.0M in hexanes) (185 μl, 0.185 mmol) was added to a solution of 4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzonitrile (59.6 mg, 0.169 mmol) in DCM (2.7 mL) at 25° C., and the resulting solution was stirred at 25° C. for 45 min. Sat. aq. Na/K tartrate solution (3.0 mL) was added, and the resulting mixture was vigorously stirred for 15 min, then partitioned between DCM (40 mL) and sat. aq. Na/K tartrate solution (10 mL). The organic layer was separated, and the aqueous layer was extracted with DCM. The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-100% EtOAc/Hexanes) provided 4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde as a light yellow solid. MS (ESI) m/z: Calculated: 356.1; Observed: 357.1 (M++1).

Workup

  1. stirringthe resulting mixture was vigorously stirred for 15 min
  2. custompartitioned between DCM (40 mL) and sat. aq. Na/K tartrate solution (10 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with DCM
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customChromatographic purification of the residue (silica gel, 0-100% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-e038ce7cd8904649962cfcd546d09d44
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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